Looking for a West Coast road trip that features unbelievable waterfalls, coastal villages, wineries, redwoods, or volcanic geological sights? Look no further–a multi-day drive from San Francisco to Portland is calling your name!

A San Francisco to Portland road trip is not for the faint of heart. It requires real dedication and the “drive” to travel slow, stop and smell the roses, and explore new sights. If you’re up for it, then you’re in the right place!

This post will serve as your ultimate guide to the San Francisco to Portland road trip. I’ll give you pointers on how many days you’ll need to complete the trip, which routes you can consider, and what notable stops/attractions are along the way.

Of course, if you’re departing from Portland for San Francisco, this post still applies to you! Just reverse the order of the spots you like to visit from this list.

*Please note: This post may contain affiliate links. You won’t be paying a cent more, but in the event of a sale, the small affiliate commission I receive will help keep this blog running/pumping out useful content. Thanks!

Don’t have time to read about all 50 stops you could potentially make along this epic drive? I’ve put together a condensed, printable version of this post with my top recommendations on the towns you should be stopping in, the parks you should be visiting, and which hotels to stay in along the way!

It’s 100% free to grab — just enter your deets below!

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SAN FRANCISCO TO PORTLAND ROAD TRIP – HOW MANY DAYS?

For the best chances to see as much as you can and make all the stops that you want, I’d recommend at least 5 days on the road for your San Francisco to Portland road trip. If you can swing a week for this trip, that would be the most ideal.

You’ll see why as soon as you start diving into the list of possible stops along your drive–my list is extensive!

This will mean making no more than 3-4 stops in a day and also finding overnight stays in smaller towns along the way. In fact, staying in smaller towns that you’ve never even heard of is what makes road-tripping so fun and spontaneous. Who knows, you might even discover a few new charming towns and cozy eateries along the way.

Instead of driving up to a hotel and seeing if they have vacancies (I know this method is not for me, the unknown would cause me too much anxiety), try searching and booking a hotel 1-2 days in advance using HotelTonight or Priceline Express Deals.

You can get some pretty great deals on last-minute bookings on Priceline if you know what you’re doing. If you enjoy the spontaneity of not knowing where or which town you’ll lay your head for the night, then don’t book anything in advance and embrace the unknown!

Before we get into the meat of it, let’s start by preparing for your road trip.

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SAN FRANCISCO TO PORTLAND – TRANSPORTATION

A durable and reliable car is a must for a road trip of this size. Our personal cars were old and by no means would we ever consider them reliable, so we ended up booking a one-way rental car for our trip. This ended up being a blessing in disguise because I discovered my new favorite way to take a road trip…

Rent a car for a one-way drive, drop it off, and fly back home once you’re done exploring. For me, I find that driving the same route back is too time-consuming and boring unless I’m taking a completely new route on the way home.

When doing this, be mindful that many car rental companies charge a one-way dropoff fee. When doing your rental car comparison, be on the lookout for what that fee looks like in your total cost. It may be $0, or it may be $150 or even more.

Rentalcars.com is our go-to these days! They’re the world’s largest online car rental service and help you compare prices of all the rental car companies out there.

Not only does the tool allow you to compare rental car prices across the major rental car companies, but most of the time you can book with no prepayment and no cancellation fees. You’ll only be charged if you show up to pick up the car.

Regardless of which rental car company you decide to go with, make sure you have the appropriate car rental coverage. Our credit card benefits typically cover car rental insurance, so we usually stick with that as our primary insurance.

If you don’t mind the drive there and back or the wear-and-tear on your car, then taking your own car is a perfectly good option too.

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SAN FRANCISCO TO PORTLAND ROAD TRIP – 5 POSSIBLE ROUTES

As with many road trips, the shortest path is hardly ever the most enjoyable. Oftentimes, you go through the countryside and sparsely populated farming towns with nothing much to see for hundreds and hundreds of miles (for example: taking the I-5 from San Francisco to Los Angeles… boring.)

Since I’m sure you want to see the best that California and Oregon have to offer, I’ve provided you with a few alternative driving routes that are far more enjoyable.

The first three routes below will provide you with a large variety of sights to see, all ranging around 600-700 miles one-way.

Route 1: San Francisco to Portland via I-5 N – 10-hour drive time

• The shortest route you could possibly take to complete the drive
• Featuring Mt. Shasta, Burney Falls, and Lassen Volcanic National Park in California, as well as and Eugene, OR.
• 635 miles; ~10 hours of driving

Route 2: San Francisco to Portland via 101 N and I-5 N – 12-hour drive time

• Featuring some of the best road trip attractions in Northern California, including Humboldt County, wine country, beaches, and redwoods, as well as Eugene, OR.
• 680 miles; ~12 hours of driving

Route 3: San Francisco to Portland via I-5 N and US-97 N – 11-hour drive time

• Featuring Mt. Shasta, Burney Falls, Lassen Volcanic National Park in California, as well as the best of Central Oregon (Crater Lake National Park and Bend, OR).
• 656 miles; ~11 hours of driving

This next route option, very similar to route #2, also features California wine country and the Northern California coast, but is a tad bit longer than route #2 because I’ve added in a few stops along the way. With this one, you’ll be taking a slight detour to visit some coastal towns in Mendocino County.

Route 4: San Francisco to Portland via 101 N, CA-128 W, and I-5 N – 13-hour drive time

• Longest route of the 4 driving options
• Featuring some of the best road trip attractions in Northern California, including kitschy roadside attractions, wine country, the California coast, as well as Eugene, OR.
• 706 miles; ~13.5 hours of driving

And last but not least, the big kahuna of road trips is below!

This is considered a bonus route due mainly to the fact that not everyone can take the time off to make this drive or see all these spots, nor would they want to drive this much to get from San Francisco to Portland.

Nevertheless, this is my personal favorite San Francisco to Portland road trip route–it’s the perfect route if you’ve got the true road trip spirit within you. Why? Because you’ll get to experience a little bit of everything along the way as well as the best of each state. Highly recommended if you have the time to swing it!

Route 5: The ultimate road trip from San Francisco to Portland

• 833 miles; 16.5 hours of driving

I like to consider this the ultimate Northern California / Central Oregon road trip. Though it is the longest and most time consuming of the routes listed here, it’s also super jam-packed with charming towns, natural wonders, fine wining and dining, and various other things to see and do.

Some highlights on this route include:

• Healdsburg, CA
• Mendocino, CA
• Ferndale, CA
• Ashland, CA
• Crater Lake, OR
• Bend, OR

I know that was a lot to take in at once, but don’t worry, it’ll make more sense as you keep reading. Take a look at the list below to see what attractions and stops interest you. I’ve organized the list below into counties/regions, along with which routes will get you there.

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SAN FRANCISCO TO PORTLAND ROAD TRIP – THINGS TO SEE AND DO

This map summarizes the possible routes from SF to Portland (and vice versa) along with the best stops along that route. Just follow the route/color of choice!

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SAN FRANCISCO TO PORTLAND ROAD TRIP – THINGS TO SEE AND DO

This grand list of towns and attractions is ordered from the furthest south (San Francisco, CA) to the furthest north (Portland, OR). Pick and choose the stops that sound most fun and appealing to you–like a kid and a candy store! After all, your road should be what you make of it!

SAN FRANCISCO

Regardless of if you’re starting a road trip in San Francisco or not, this amazing city is worth exploring for a few days. If you like nature, stunning architecture, shopping, museums, kitschy/hipster bars, and exceptional food in a city with a laid-back vibe, San Francisco is a must.

If you only have a few hours to a day to explore, get some good food, and see some of the iconic spots like Fisherman’s Wharf and The Golden Gate Bridge.

If you have a weekend to spare, you can slow down a bit and really get to know some of our iconic neighborhoods such as The Mission District, Haight-Ashbury District, or North Beach / Chinatown. 

Plan for a visit to the ferry building (houses a bunch of artisan shops and restaurants, as well as an awesome farmer’s market on Saturday mornings), a trip to Alcatraz or a sunset bay cruise, and a visit to Golden Gate Park and Sutro Baths.

No matter what you decide to do here, you’re sure to have a wonderful time. Just be sure to bring layers and prepare for some unpredictable wind and fog!

Want more on SF? Here are some more helpful posts:

• 60+ Free and Affordable Things To Do In San Francisco, California
• Best San Francisco Neighborhoods To Visit (And What To Do Beyond SF)
• 3 Days In San Francisco, CA: The Perfect Weekend Itinerary
• 20 Fun Things To Do In San Francisco At Night

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MARIN COUNTY

(ROUTES 2, 4 & 5)

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MARIN HEADLANDS

TWE RECOMMENDED CHOICE

There’s so much natural beauty in the Marin Headlands area, so if you have the time, cross the Golden Gate Bridge (on bike, on foot, or by car) and get your outdoor exploration on. Check out the amazing 360-degree views from Hawk Hill, one of the highest points in the Marin Headlands.

Stop at Black Sands Beach early in the day (parking is difficult), then make your way to Point Bonita Lighthouse for more great views featuring this iconic lighthouse. In the afternoon, pack a picnic and relax at Rodeo Beach, an activity you can’t go wrong with.

Consider staying for sunset as this is one of the best places to catch it. While you can also reach the beach by car, the best way to arrive is via the coastal trail that picks up on either side of the beach.

Where To Stay: Acqua Hotel – great home base for exploring the Marin/Mount Tamalpais area!

TENNESSEE VALLEY

Check out the local hidden gem that is Tennessee Valley if you’re looking to experience a semi-hidden beach/cove with gorgeous views!

Tennessee Valley meanders for approximately two miles through serene, rolling hills down to the Pacific Ocean. At the end of the trail, you’ll reach a very pretty beach that’s perfect for picnicking and sunbathing!

The 1.8-mile, well-paved trail to Tennessee Cove begins at the trailhead parking lot, about a mile down Tennessee Valley Road. The trails connect to other parks along the coast like Muir Beach to the north and Rodeo Beach to the south.

Pro Tip: This trail has become pretty popular, especially on weekends! Arrive early or be prepared to hunt for parking along the street (as the parking lot fills up fast).

MUIR WOODS NATIONAL MONUMENT

If you’re short on time and can only make one stop to see redwoods, you can check out Muir Woods National Monument. While this is certainly a very scenic spot, there is a steep entry fee and you’ll need to reserve a vehicle parking space. Learn more about reservations and fees here.

Unfortunately, Muir Woods draws extreme crowds during peak season, which doesn’t elicit the usual peaceful ambiance you get when among the trees.

As an alternative (and what I usually do)– you can choose to take an alternative hike where the trail crosses through Muir Woods National Monument. That way, you won’t have to deal with traffic, parking, or paying that overpriced entry fee.

STINSON BEACH / MOUNT TAMALPAIS

TWE RECOMMENDED CHOICE

Stinson Beach is one of northern California’s most popular beach towns, conveniently located just off CA Hwy 1 about 20 miles north of San Francisco.

The wide, pristine stretch of sand runs for almost 3 miles and is known to be great for surfing, kayaking, and even swimming (it’s been noted to be slightly warmer than other Northern California beaches, which are always cold).

The town of Stinson Beach is a really cool place to visit before or after hiking around the area. You can take it slow and grab breakfast/lunch, explore the art galleries, hit the beach, or embark on a hike! Muir Woods, Mount Tamalpais, and Alamere Falls are all iconic hiking spots just a short drive away.

One of my all-time favorite hikes: the 6.8-mile Dipsea, Steep Ravine, and Matt Davis Loop. The views throughout the entire hike are some of the best in the Bay Area!

For something that’s half the length but equally as beautiful, opt for the 3.7-mile Dipsea to Steep Ravine Loop from Pantoll Campground.

My favorite way to start any hike in this area: with a decadent, freshly baked pastry from the bakery stand outside of Parkside Cafe. In the ‘downtown’ area, you will find a few shops, art galleries, cafes, and markets, as well as some cute bed & breakfast options.

Where To Stay In The Stinson/Mill Valley Area: Mill Valley Inn

BOLINAS

One of the best reasons to visit Bolinas is the 13-mile out-and-back Alamere Falls hike.

On this hike, you’ll enjoy stunning views of the coast, combined with varying terrain through forests and tall brush, ending at a beautiful and rare waterfall plummeting 40ft into the ocean. If you’re lucky enough to do this hike during the summer, you can even take a swim in Bass Lake on the way back to the trailhead.

Back in town, take in the sights of civilization– stroll the streets and make stops at all the bookstores, cafes, and art galleries as the locals do. For food and drinks, check out Coast Café and Smiley’s Schooner Saloon and Hotel.

Other notable places to grab food: if you love oysters, then you’ve come to the right place. Tomales Bay Oyster Company and Hog Island Oyster Co. are absolute musts.

Where To Stay In Bolinas: Smiley’s Saloon & Hotel

POINT REYES

TWE RECOMMENDED CHOICE

Famous for the National Seashore, Point Reyes is a semi-hidden gem in Marin County. Hiking, horseback riding, kayaking, and clamming are just some of the activities that attract local day-trippers, as well as checking out restaurants and browsing bookstores in the sleepy town center.

Start your day trip to Point Reyes National Seashore at Point Reyes Lighthouse, perched on the western headlands. If you want to get up close and personal, climb down a few hundred steps to check it out, then climb right back up.

Next, catch a glimpse of the California elephant seals over the sea cliffs anywhere along the seashore. Want to see herds of elk in their natural habitat? Take a hike to the Tule Elk Reserve beginning at the Tomales Point Trailhead.

Point Reyes Station, in the actual town area of Point Reyes, has become a popular spot in recent years. There’s a huge focus on sustainable agriculture, locally produced artisanal foods, and outdoor activities.

In the summer to early fall, you can catch the Point Reyes Farmers’ Market, running on Saturdays from 9 am to 1 pm at Toby’s Feed Barn. It’s not the largest farmer’s market, but it sure is a great opportunity to check out the local artisans, dairy farm products (cheeses and butters), and bakeries.

Our favorite bakery in town? Definitely Brickmaiden Breads!

Where To Stay In Point Reyes: Olema House

Read More: Point Reyes Day Trip Itinerary: The Perfect Weekend Adventure

BODEGA BAY

Bodega Bay is jam-packed with hiking and biking trails that offer those stunning Pacific Coast views. It’s also one of the West Coast’s premier whale-watching spots! The whales can be spotted almost all year long, but the best chances will be during primary migrations (October through April).

Interested in horseback riding? Well no-brainer, the coastal views of Bodega Bay make for a wonderful backdrop.

Bodega Bay and the surrounding area is also a foodie’s paradise —  fresh oysters and seafood are not to be missed here. Make sure to stop at Bodega Bay Oyster Company on your way in/out of town to try some of the freshest oysters in the area.

If you’re not looking for anything fancy or fishy, check out Drakes Sonoma Coast Kitchen for breakfast, or head to Spud Point Crab Company for their famous crab chowder.

Where To Stay In Bodega Bay: The Inn at the Tides (mid-priced option) or The Lodge at Bodega Bay (splurge option)

HEALDSBURG

TWE RECOMMENDED CHOICE

Hop on the 101-N and cruise up to Healdsburg, a town offering a less touristy but equally memorable wine country experience.

Healdsburg is a small, charming town filled with modern amenities as well as an abundance of world-class wineries and farm-to-table restaurants. It’s the perfect base for exploring the countryside of lush valleys and redwood forests that surround Lake Sonoma and the Russian River.

It’s structured similarly to the city of Sonoma, with its historic downtown dotted with art galleries, tasting rooms, eateries ranging from super-casual to fine dining, boutiques, and kitschy antique shops.

As a stop to a longer road trip, expect to spend about 2-3 hours walking around and browsing all the town has to offer before hitting the road again. Given the large variety of bed & breakfasts/hotels here, Healdsburg will provide you with an unforgettable overnight experience. Opt to stay downtown, as you’ll be within walking distance of the many restaurants, bars, and shops surrounding the main plaza.

Now let’s discuss the wine and the food.

Wine: The city of Healdsburg is surrounded by an array of great wineries within the Alexander Valley and Dry Creek Valley wine regions. If you’re looking for something more conveniently located in the city, check out the tasting rooms Banshee or La Crema.

Food: To start your day off, stop in to Flying Goat Coffee in downtown Healdsburg for some of the best coffee in town. Hungry? Grab a table at the New Orleans-inspired breakfast spot, The New Parish, serving up beignets overloaded with powdered sugar…as they should be. Other recommended options for eats include Chalkboard (small plates), Bravas (tapas), and Madrona Manor (for that special occasion fine dining meal).

Where To Stay In Healdsburg: H2hotel, Healdsburg Inn on the Plaza or Hotel Les Mars (if it’s in your budget!)

Looking for more of an adventurous stay? Consider glamping at Wildhaven Sonoma Glamping!

GEYSERVILLE

In terms of a formal downtown to explore, there really isn’t much here as it is comprised of only one tiny block worth of establishments. But please don’t let that be a reason for overlooking this gem of an area!

In Geyserville’s surrounding countryside (and this is where Geyserville really shines), you’ll find many award-winning wineries, excellent B&Bs and inns, countless opportunities for outdoor adventure, and even a modern casino.

For convenient wine tasting, check out Locals— they carry a ton of varietals and love teaching and talking about wine. Make sure you check out one of the best Italian restaurants I’ve experienced in the United States, Diavola Pizzeria and Salumeria–Michelin quality food for very very affordable prices. Seriously some of the best Italian-style pizza I think I’ve ever had (and I spent a whole month in Italy!).

If you’re limited on time and want to do some wine tasting, definitely check out the picturesque Ferrari-Carano Vineyards for the complete wine country experience (good wine, good vibes, beautiful scenery).

Where To Stay In Geyserville: Geyserville Inn

CLOVERDALE

Another quaint wine-tasting town! Cloverdale is a small town seated on the banks of the Russian River. Family-oriented and down-to-earth, this Northern Sonoma County river town is a charming stop for those looking to explore the nearby Alexander and Dry Creek Valleys.

From the first impression, you’ll notice a very well-maintained town with charming little houses and colorful gardens surrounding the downtown area. Art galleries, eclectic gift shops, and restaurants make up this lively part of town. You’ll then notice random art sculptures everywhere; Cloverdale is part of a public nine-mile Sculpture Trail (in conjunction with Geyserville), a display of outdoor sculptures in and between the two towns.

Like many other small towns in Sonoma County, tasting rooms are speckled throughout its main streets. Head to nearby Dry Creek Valley to taste hand-crafted wines at Fritz Underground Winery and enjoy the beautiful scenery while you’re at it.

Where To Stay In Cloverdale: The Pinschower Inn

GUERNEVILLE

TWE RECOMMENDED CHOICE

Situated in Sonoma County’s Russian River Valley lies a little town named Guerneville. Guerneville is a rustic and quirky town, popular for summer getaways and river activities. It’s had a long history, beginning as a logging town to now a summer resort destination.

Another plus? There’s a growing dining scene here. If you’re able to spend time in this casual and funky town, be prepared to have a great time outdoors and indoors alike.

Spend the afternoon relaxing next to the river at Johnson’s Beach (a local favorite). There you’ll find a spacious stretch of pebble beach surrounded by those majestic redwoods this region is famous for.

Don’t forget your pool floaty– hanging out on the river is a million times more fun with one than without one. If you do forget, don’t fret, there’s more to do in the water. There are rentable beach chairs, canoes, kayaks, and pedal boats.

As for food, Boon Eat + Drink is a must-try, near Big Bottom Market (they have the best biscuits ever, so go there too if you can). For drinks, check out El Barrio bar, serving up tequila, mezcal, and bourbon, a healthy break from all the wine in this region.

Where To Stay In Guerneville: We personally love the rustic vibes at Highlands Resort! For an extra unique stay, see if you can snag a night or two at Autocamp, hosting a stylish collection of hipster Airstream trailers and luxurious glamping tents.

ARMSTRONG REDWOODS STATE NATURAL PRESERVE

If you’re looking for a few hours’ escape from the hustle and bustle of civilization, Armstrong Redwoods State Natural Reserve is the perfect road trip stop for you.

Located just north of the Russian River in a canyon 2 miles from Guerneville’s Main Street, this stunning reserve offers a quieter experience with fewer crowds, allowing you to fully immerse yourself in the pristine beauty of the redwoods.

One of the highlights of Armstrong Redwoods State Natural Reserve is the towering redwoods themselves. These ancient trees, some of which are over a thousand years old, are a sight you’ve gotta see with your own eyes.

If you’re limited on time, the must-do trail here is the Armstrong Redwoods Grove Loop Trail. For something a bit longer, take on the 5-mile East Ridge and Pool Ridge Loop Trail!

You’ll feel like you’ve stepped into a fairytale forest as you hike through the lush greenery, surrounded by ferns and a moss-covered forest floor. It’s got Lord Of The Rings vibes all the way!

And if you’re looking for a peaceful retreat after your stroll, the park’s picnic areas offer the perfect spot to relax and take in all the relaxing vibes.

FORESTVILLE

A summer destination for bohemians, artists, and vacationers since the 1900s, this tiny town has all you need for a laidback natural retreat — the Russian River at your feet, the majestic forest spanning more than the eye can see, and a quaint town full of local flavor.

If you do go through Forestville, it is totally worth your time to pick up a few loaves of bread at Nightingale Bakery (favorites include the potato rosemary roll and chocolate chunk brioche). For breakfast, stop by the Russian River Pub. This local spot serves up seriously good eats, from crab cake Benedict to the homemade Irish soda french toast.

Canoe or kayak down the Russian River or just relax by one of the many beaches in the area– Steelhead Beach, Sunset Beach, and Mom’s Beach. If you’re looking for an outdoor adventure on wheels, bike the West County Trail through vineyards and orchards (a 5.57-mile flat, paved trail).

And of course, you can’t miss Front Street, the hippie, laid-back ‘downtown’ area of Forestville.

SANTA ROSA

Santa Rosa, the urban center of Sonoma County, may not be the first place you’d think of visiting when in wine country, but this North Coast city offers more than meets the eye. This up-and-coming city is evolving to be a wining and dining mecca, similar to other cities in Sonoma County!

It’s the perfect destination for people who want to spend their day wine tasting and engaging in outdoor adventures and their nights enjoying the arts as well as Michelin-starred restaurants. End your night with ice cream at Noble Folk— they make the absolute best cookies and cream ice cream ever, no joke.

Let’s start with the wine. Easily one of the most beautiful wineries in Sonoma Valley, Matanzas Creek specializes in Merlot, Chardonnay, Sauvignon Blanc, and Syrah wines. The beautifully landscaped visiting area is a treat in itself, but don’t miss the Vintage Room, which hosts private tastings and cheese pairings. You really can’t go wrong with this experience.

Outside of wine tasting, check out the wildlife preserve Safari West, where you can experience close to 700 animals in conditions close to their natural African habitat (animals range from gazelles, zebras, cheetahs, antelopes, cape buffalo, wildebeests, and giraffes).

Looking for aerial views instead? Given the varied views of this region (grapevines, coastal views, rolling hills), hot air ballooning is also a popular activity here.

Interested in a wine tasting tour without the hassle of driving? Book this Private Sonoma or Napa Wine Tours with Concierge Service.

Where To Stay In Santa Rosa: Hyatt Regency Sonoma Wine Country or Vintners Resort

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MENDOCINO COUNTY

(ROUTES 4 & 5)

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Mendocino County is a picturesque region that showcases some of the most stunning natural landscapes that California has to offer. Located 163 miles north of San Francisco, it takes about three hours to get there. Though a lot of the drive is on windy terrain, the cliffs, crashing waves, and adjacent green wilderness make for an unforgettable road trip. 

With over 90 miles of Pacific coastline, various state parks, countless redwood trees, and a treasure trove of things to do, here is my roundup of Mendocino’s most notable places to visit.

BOONVILLE

Welcome to the first stop of Mendocino County! Boonville is known as the hot spot on the road to the coast. Anderson Valley Brewing Company (great beer) and Pennyroyal Farms (award-winning cheese as well as wine) are notable stops here. Boonville is also home to winery tasting rooms, shops, and galleries.

While the beer-drinking crowd will enjoy Anderson Valley Brewing, this region is best for wine lovers, especially fans of pinot noir and chardonnay. Navarro Winery, Husch, and Toulouse are good starting points. For those looking to spend the night, there are lots of bed & breakfast options here. Stay at Boonville Hotel or the stylish hotel called The Madrones, a small compound that offers on-site tasting rooms– how cool is that!

For a great spot to eat: enjoy a farm-to-table feast at The Bewildered Pig.

VAN DAMME STATE PARK

TWE RECOMMENDED CHOICE

Van Damme State Park is a great, relaxing spot for outdoor activity and overnight camping. It’s also the perfect location to enjoy a small beach, a creekside hike, and the unspoiled forest!

Hands down, the best trail to do in this park is the Fern Canyon Trail. It’s one of the lushest and green trails I’ve ever experienced in California, so if you want to be transported to “Jurassic Park” times, I’d highly recommend doing a portion, if not the whole 8.3 mile hike.

At the end of the trail, you can continue on to see the Pygmy Forest, showcased by a raised boardwalk winds through a thicket of stunted century-old trees no more than 10 feet tall.

Head across the street to Van Damme Beach, famous for abalone diving. Though abalone diving and catching will be restricted until their population restores over the next few years, it’s still a super cool and convenient beach to check out (especially for sunset).

Note: There can be mosquitoes here, so don’t make the mistake of forgetting insect repellent.

FORT BRAGG

Fort Bragg’s Glass Beach, seemingly covered in gems, is the result of decades of broken bottles, windows, and car taillights littering the area. These useless particles have naturally transformed into beachcombing treasures covering the beach. Hike down the smaller cliffs to the main parts of Glass Beach to check out the sea life and tidepools that exist here. It’s quite a sight to see.

The downtown area by Main Street is the best spot to grab breakfast/lunch. We love Eggheads Restaurant, a fun family-owned restaurant adorned in Wizard of Oz photos and murals. Follow up your meal with a stroll through town, popping into the various gift shops, boutiques, and general stores.

Explore MacKerricher State Park if you want to see seals and migrating whales. Stop at photo-worthy Point Cabrillo Light Station State Historic Park and the sprawling Mendocino Coast Botanical Gardens as you head north.

Where To Stay In Fort Bragg: If you’re in need of a place to stay in Mendocino County, the iconic Inn at Newport Ranch should be your first option if it’s within budget. Set on a 2000-acre coastal cattle ranch, the Inn is your ultimate escape from reality. Surrounded by epic ocean views and redwood trees, the property consists of over 20 miles of private trails perfect for strolling, hiking, or horseback riding.

POINT ARENA

For those of you who love animals or wish to travel to Africa, this one is for you. One of the most fascinating attractions in Mendocino is the amazing B. Bryan Preserve, dedicated to the livelihood of endangered African animals (giraffes, zebras, antelope, etc).

This is not a zoo, it’s actually a million times better. The guided vehicle tour is close to an African safari as you’re going to get on this side of the world. The tour itself is fantastic, educational, and completely worth your time and money.

Point Arena Lighthouse is also a picturesque landmark you can check out. Thanks to the backdrop of the Pacific Ocean and the rugged coastline, photos of the lighthouse end up looking unreal. To get to the top, it’s 145 steps up a classic spiral staircase, making it structure the tallest lighthouse on the West Coast.

MENDOCINO

TWE RECOMMENDED CHOICE

Visit the Victorian-esque town of Mendocino, and trust that it will be quaint, sleepy, and romantic all that the same time. You’ll come across spas, boutiques, gift shops, and chocolate shops, all of which tend to close around 5pm. What did I tell you about this town being sleepy?

After the shops close, take a stroll on the trails overlooking the cliffs as well as through the neighborhood to see all the houses with impeccably groomed colorful gardens.

You could easily spend a day exploring the town’s numerous art galleries, but if you visit only one, make it the Mendocino Art Center. This spacious gallery exhibits a revolving selection of local and national artists. It also offers more than 150 retreat-style classes each year in subjects such as ceramics, jewelry and sculpture. How cool is that?

For breakfast or lunch, check out the popular local hangout the Goodlife Cafe, serving an irresistible range of homemade soups, sandwiches, pastries as well as very well-made coffee. Have dinner at Fogeater Cafe, a cheerful vegetarian restaurant, or Cafe Beaujolais, serving up French cuisine in a Victorian farmhouse (a fine dining staple here).

Of course, romantic and casual B&B options are plentiful here for those looking to spend a night or two.

Where To Stay In Mendocino: Blue Door Inns, Four Sisters Collection or Agate Cove Inn

101 NORTH ROADSIDE STOPS

TWE RECOMMENDED CHOICE

Confusion Hill (Leggett)

Confusion Hill is a prime example of roadside attraction magic. Kitschy, eclectic, and amusing all at the same time, this California State Point of Historical Interest has been attracting road-trippers since 1949. It features a gravity-defying house, Redwood Shoe house, mountain train ride, and the world’s largest standing chainsaw sculpture.

Confused and intrigued? Maybe, maybe not. If nothing more, at least stop here to stretch your legs if you’re passing through. The gravity house here rivals the more famous one in Santa Cruz (Mystery Spot), but for a fraction of the cost. There is a gift shop and snack bar here as well.

Chandelier Drive-Thru Tree (Leggett)

Chandelier Drive-Through Tree in Leggett is a privately-owned attraction that charges a $10 admission fee. It’s super close to Confusion Hill. Most visitors who pay the admission to drive through the tree say this one is the best in Northern California. Standing at an estimated 315 feet high and 21 feet in diameter, this 2400-year-old tree is a real sight to see.

Whether you drive through it or simply walk by it, seeing the size of it is truly incredible, to say the least. Looking to pick up some souvenirs? The gift shop sells pieces of live redwood trees to grow at your own at home, among other redwood trinkets you’re not likely to find anywhere else.

Legend of Bigfoot (Garberville)

Looking for a museum all about the history of bigfoot? Well, look again. This is actually a half-outdoor half-indoor store selling a mixed bag of stuff. Most of the products and gifts are bigfoot related, but they also sold jams and honey, clothing, themed garden sculptures, and outdoor decor. Unfortunately, you will not learn anything about Bigfoot, but it’s still a cool stop with pretty decent photo ops!

AVENUE OF THE GIANTS

TWE RECOMMENDED CHOICE

Instead of continuing straight on the 101 North to reach Eureka, take the 31-mile alternative scenic route through the Avenue of the Giants. Surrounded by Humboldt Redwoods State Park, this world-famous scenic drive is by far the most outstanding display of giant trees in the California redwood belt.

What a beautiful drive, to say the least. The best part is, it’s a free self-guided driving tour (with both a North and a South entrance and 8 specific stopping points). Dedicate a few hours here–stop at a few of the groves and enjoy your presence among the trees. If you’re limited on time, I’d recommend the Founder’s Grove.

Pro Tip: Don’t rush it. Take your time soaking in the sights and sensations. Pack a picnic and spend some time in one of the groves really enjoying the connection with nature. It’s the perfect place to disconnect from the hustle and bustle of everyday life.

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HUMBOLDT COUNTY

(ROUTES 2, 4 & 5)

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At least once in your lifetime, you need to visit the magnificent coastal redwoods of Humboldt County.

Whether you enjoy taking scenic drives or hiking trails, you’ll find plenty of choices here, as it’s home to the Redwood National & State Parks in the north county and the Avenue of the Giants and Humboldt Redwoods State Park in the south county.

Not to mention all the other various parks, forests, preserves and beaches, making Humboldt County a paradise for nature lovers and outdoor enthusiasts alike!

EUREKA

A portion of Eureka, mainly the historical downtown, is actually really quaint, but the other half is sort of rough (I’d recommend just stopping by and checking out Old Town). Old Town Eureka is chock-full of restaurants, antique shops, clothing and lifestyle/gift shops, and art galleries. It’s a great place for a 1-2 hour stroll.

If you’re passing through and looking to make a pit stop for food, check out Los Bagels in Old Town, Siam Orchid Thai Cuisine, as well as Samoa Cookhouse minutes away from Eureka, the last surviving cookhouse in the West serving up a fixed buffet menu that changes daily.

Though the city can have a bit of a transient feel, the food certainly does not disappoint! If you’re looking for a charming place to stay, there are a handful of historical Victorian B&B’s to pick from.

Where To Stay In Eureka: Carter House Inns or Best Western Plus Humboldt Bay Inn

FERNDALE

TWE RECOMMENDED CHOICE

Who knew there would be such a picturesque Victorian village nestled deep in the redwoods, just 20 miles from Eureka, CA? With its fantastically preserved Victorians, vibrant small-town charm, and history as a filming location for major movies, Ferndale, is the perfect stop when in the Lost Coast area.

Stroll along Main Street, where art galleries, general stores, and boutiques complement an array of Victorian architecture. In my opinion, Ferndale tops the charts on small towns to visit along the coast and is 100% worth a stop.

You definitely cannot miss Golden Gait Merchantile. Named one of America’s most charming general store by Country Living, this store sells something for everyone–from candy, cookware, and antiques to local and imported specialty foods, jewelry, and stationery. It’s hard not to feel like you’ve stepped back in time; the western general store vibe really makes it a cool place to just check out.

Don’t miss the upstairs museum while you’re there (there are Victorian mannequins, so cool)!

Where To Stay In Ferndale: Gingerbread Mansion – easily the most charming hotel in this entire post!

ARCATA

Arcata is a super short drive from Eureka, but feels worlds away. Arcata’s beginnings go back to the Gold Rush when it was a shipping and supply center for the miners on the Trinity River. Today, sprawling over the hillside above Arcata, Humboldt State University dominates the city and promotes a youthful, artistic and intellectual ambiance.

Check out the main plaza, where lots of restaurants and shops reside. There’s an impressive lawn of grass situated smack dab in the middle of the plaza, making it a super chill place to hang out, sunbathe, and watch people pass by.

The town also contains many restored Victorian homes–driving or walking, getting lost in the neighborhoods of Arcata is not time wasted. Looking for something else? The Arcata Marsh & Wildlife Sanctuary offers quiet trails and superb birdwatching.

Where To Stay In Arcata: Hotel Arcata

SUE-MEG STATE PARK (PATRICK POINT STATE PARK)

TWE RECOMMENDED CHOICE

Located near Trinidad, California way up north, Sue-Meg State Park (formerly known as Pactrick’s Point SP) is a must-visit for anyone looking to explore the untouched beauty of Northern California and immerse themselves in the tranquility of nature.

What a lush and sprawling state park to visit! One of the main reasons to stop at Sue-meg SP is Agate Beach–it’s a beachcomber’s paradise. Agate Beach is two miles of solitude and splendor with awesome beachcombing opportunities.

On any given day, you can find a variety of rare rocks, such as jasper, agate, and even jade (hence, its name).  Collecting stones at Agate Beach is allowed, but visitors are limited to one armload per person.

To get to the beach, make sure to wear relatively sturdy shoes; you’ll have to take a decently long/curvy trail down from the parking area.

For a nice hiking activity that’ll get your heart thumping just a bit, try out the 3.1-mile Patrick’s Point Rim Trail. After that, set up camp and enjoy the ocean breeze over the campfire!

Where To Stay: Sue-meg State Park Campground

PRAIRIE CREEK STATE PARK

Situated just a short drive from Sue-Meg State Park, Prairie Creek State Park is a nature lover’s paradise that promises to take your breath away.

Prairie Creek SP is the perfect spot for those with limited time. Reserve half a day for your visit — perhaps after a visit to Sue Meg State Park — and you won’t be sorry! The main attraction here? The Fern Canyon Loop Trail. 

This hike really cannot be missed. It is hands down one of the most beautiful places in California I had ever laid my eyes on!

Here, you’ll have countless opportunities to see elk, streams/river crossings, massive canyon walls covered with foliage, and stunning redwoods. Take a drive on the Newton B. Drury Scenic Parkway, which will be an eye-capturing adventure in itself.

In minutes, you’ll be enveloped in beautiful groves of mature redwoods lining the road. Trailheads appeared approximately every half-mile, so select some at random and explore different parts of the park for a few hours.

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SISKIYOU COUNTY

(ROUTES 1 & 3)

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LASSEN VOLCANIC NATIONAL PARK

Lassen Volcanic National Park is one of California’s lesser-known national parks, due mainly to its location in Northern California, but it is also one of its most fascinating. Lassen belongs to the Cascade Mountain Range and is considered one of the largest plug dome volcanoes in the world, last erupting in 1921.

Despite its name, Lassen doesn’t only feature bubbling pits of lava and volcanos—it has some awesome water attractions, too. This park has everything from volcanic summits to geothermal areas and stellar waterfalls.

It is a must-visit when passing through this part of California, especially if you happen to be driving by during the season when everything is more accessible from the lack of snow and ice (June/July to October/November).

While Lassen is open year-round, 24 hours a day, many facilities are only open for the summer season and road access is limited in the winter months. Notable landmarks worth stopping by here are Bumpass Hell (3-4 mile roundtrip hike), Kings Creek Falls (2.4-mile roundtrip hike), and Sulphur Works.

BURNEY FALLS

TWE RECOMMENDED CHOICE

Without question, Burney Falls is one of the most spectacular waterfalls in the state. Located in the Cascade mountains forty miles north of Lassen Volcanic National Park, you’ll find a large, everflowing set of falls fed by the melt of the surrounding mountains.

The 129ft waterfall draws many road trippers and adventurers to McArthur Burney Falls Memorial State Park all year round, even when the rest of the waterfalls in California have turned into small trickles in the summer.

There is a short 1-mile loop trail you can take after soaking in the beauty of the falls. Visitors can enjoy the interpretive signs on the nature trail and enjoy the shaded greenery of the park. The end of the trail leads you to the bottom of Burney Falls where you can experience the majestic falls up close. Parking Fee: $10 per car for entry.

Where To Stay Near Burney Falls: Shasta Pines Motel & Suites

CASTLE CRAGS STATE PARK

While a lesser-known state park in Northern California, Castle Crags State Park is such a lovely recreation area with an array of different terrain to enjoy, as well as some breathtaking views of Mount Shasta and the beautiful Shasta Valley right behind it!

Located in the Shasta Cascade region of Northern California, the park is known for its towering granite spires and rugged terrain — almost reminiscent of what you get when you visit Yosemite National Park.

By far the most popular hike in the park is the Castle Dome via Crags Trail, which takes you on a strenuous 5.8-mile round trip journey through a beautiful forest and up up up! In the end, you’ll get to soak in some truly stunning 360-degree views of the surrounding granite spires.

If you’re planning on doing this hike, bring lots more water than you think you need, and start as early as you possibly can. It gets hot super fast and you’ll be climbing up most of the time until you reach the top. Bring bug spray for the summertime!

Where To Stay For Castle Crags State Park: Inn At Mount Shasta or Mount Shasta Resort

MOUNT SHASTA

Stop in the Mount Shasta area (Siskiyou County) to experience out-of-this-world landscapes shaped more by volcanoes! What you’ll find is when you’re up here, you’re in volcano land, which means you’re going to get to experience a fascinating terrain specific to this region.

There’s so much to do outdoors here including hiking, biking, and experiencing the culture of the small towns that sit in the shadow of Mount Shasta.

One of the prettiest trails to check out is the 2-mile path along the McCloud River which leads to a trio of spectacular waterfalls (lower, middle, and upper falls). Definitely worth checking out if you love chasing waterfalls.

Depending on what time of year you visit Siskiyou County, you can choose to go hiking or skiing on the mountain. The Mount Shasta area is a good place to make your home base if you plan on exploring Lassen Volcanic National Park, Castle Crags State Park, and Burney Falls.

Where To Stay In Mount Shasta: Inn At Mount Shasta or Mount Shasta Resort

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CENTRAL OREGON

(ROUTES 3 & 5)

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CRATER LAKE NATIONAL PARK

TWE RECOMMENDED CHOICE

How can you resist a national park when you’re on a road trip? I certainly can’t! Crater Lake National Park was established in 1902 and is the only national park in Oregon. The park encompasses the caldera of Crater Lake, a remnant of Mount Mazama (a destroyed volcano), and the surrounding hills and forests.

The biggest reason to come here is to feast your eyes on the lake, clocking in at 1,949 feet (594 m) deep at its deepest point. Crater Lake takes the cake for being the deepest lake in the United States and the second-deepest in North America. During your entire time here, you’ll be wondering how is it so blue?

Upon arrival, head towards the visitor’s center, which also serves as the start of a few good hikes. We recommend checking out the Discovery Point Trail, which is an easy 4.0-mile walk with stunning lake views the entire time. This makes for a great intro hike before exploring the rest of the park. If you love chasing sunrises, try getting to Crater Lake National Park before sunrise. Sunrise on Watchman Peak is epic!

After a picnic lunch at one of the many amazing viewpoints, head down the Cleetwood Cove Trail (1.8 miles roundtrip) to access the lake for a cold, refreshing swim and some unforgettable cliff jumping! For more varied scenery that doesn’t involve staring into the lake, check out the Pinnacles Overlook Trail and Plaikni Falls.

Where To Stay Near Crater Lake: Crater Lake Resort

CASCADE LAKES SCENIC BYWAY

TWE RECOMMENDED CHOICE

The Cascade Lakes Scenic Byway is a historic highway that starts on Century Drive in Bend and winds its way through 66 miles of towering mountain peaks and lakefront vistas. The route offers stunning mountain views including Mt. Bachelor, Broken Top, and South Sister.

Stop along the way at one of 14 alpine lakes in the area to enjoy various recreational activities. You can go fishing at Hosmer Lake, rent a standup paddleboard or boat to explore Elk Lake or Cultus Lake or stop for a hike with epic views of Devil’s Lake. The byway is open late spring through fall, but some sections are closed during the winter months due to snow.

NEWBERRY CRATER

Exploring the Newberry Crater is a great way to learn about the geological history that helped make Central Oregon the beautiful place it is. Once you’re in the Newberry National Volcanic Monument area, visiting Lava Lands Visitors Center is a perfect way to get oriented before you head to Newberry Crater.

Stop at Paulina Falls, an 80-foot double waterfall located only a short walk from your car. From there, check out Paulina Lake, a lake area complete with a lodge, restaurant, and watercraft rentals.

LAVA RIVER CAVE

After you’re done exploring Newberry Crater, check out Lava River Cave! The lava tube is over 5,200 feet long, and since it hovers around 42 degrees Fahrenheit year-round, you’ll definitely need a puffy jacket to keep you warm.

Once you descend down 100 steps into the darkness, then hike a mile each way to explore this massive lava tube. Ice stalactites hang from the ceilings even during the summer season, giving it that out-of-this-world feel. If you are looking for fun things to do with kids, this is a great place to explore.

Since it’s dark and the ground is uneven, be sure to have sturdy shoes and two light sources with you (headlamp, flashlight, or lantern– your phone won’t cut it). If you don’t have an adequate light source with you, the Forest Service will rent one to you.

SUNRIVER

TWE RECOMMENDED CHOICE

After leaving the Crater Lake National Park area, you can choose to stop at Sunriver, OR for some quick shopping and strolling. At the very least, you can treat it as a pitstop and stretch your legs here!

Sunriver is a neighboring town located south of Bend on the Deschutes River. It serves as Central Oregon’s premiere retreat, resort, and residential community. As such, you can expect there will be lots of resorts and lots of things to do!

Aside from luxury condos and river-view lodges with unforgettable spas, you can also find world-class golfing, 35+ miles of paved biking trails, horseback riding, and family fun at a waterpark.

Don’t have enough time for outdoor activities? There’s also an awesome shopping/dining area called The Village at Sunriver where you can shop and eat tax-free! In the wintertime, they have ice skating here as well. If you’re looking to try some craft beer, don’t miss Sunriver Brewing.

Where To Stay In Sunriver: Sunriver Resort

BEND

TWE RECOMMENDED CHOICE

If you’re going to be driving through Central Oregon, you absolutely have to stop in Bend. If you didn’t know, Bend, Oregon is an absolute outdoor haven all year round. Summers are ideal for hiking, biking, rock climbing, and water sports, while winters are perfect for skiing or snowboarding on Mt. Bachelor.

It’s the ultimate land of outdoor adventure, and you can’t forget about the craft beer tasting! Seriously, the sheer amount of fun you can have here is unreal. There’s a lot to do within the city limits and even more to do outside of them.

Check out our full list of 25+ things to do in Bend here!

Where To Stay In Bend: LOGE Bend or Riverhouse on the Deschutes 

Read More: 25+ Fun and Exciting Things To Do In Bend, Oregon

REDMOND

Redmond is a hub in the high desert along the 26 with a rejuvenated downtown, a growing beer scene, and lots of recreational activities to enjoy.

Head to Downtown Redmond for a light stroll among fine dining restaurants, boutiques, bookstores, and cafes. You’ll also find a few great breweries in Redmond including Kobold, Initiative, Cascade Lakes, and Wild Ride.

For family-friendly fun, check out Splash Park or the ice rink in the heart of the city. Near the airport is the Deschutes Fair & Expo Center, which hosts a wide range of events, concerts, trade shows, automobile shows, and more. Redmond is also where the Deschutes County Fair & Rodeo is held in August.

Where To Stay In Redmond: SCP Redmond Hotel

CRESCENT MOON ALPACA RANCH

I added this to the list in hopes that anyone reading this is also in love with alpacas as much as I am. At the alpaca ranch, you’ll get the chance to feed the adorable alpaca as well as enjoy the alpaca boutique. It’s only 8 minutes away from Smith Rock, how can you say no?

It’s a fun place to stop, especially if you love animals or are traveling with children. You can expect to spend 45 minutes to 1 hour here. We missed this on our last road trip, but we’re definitely making it a priority the next time we road trip to Bend, OR.

SMITH ROCK STATE PARK

If you enjoy scenic views of towering canyons or rock climbing, Smith Rock State Park is the place for you. Rock climbers from all over the country flock to Smith Rock State Park to experience the thousands of climbing routes in the park. Here you’ll find dynamic routes that are ideal for various types of climbing and bouldering.

If climbing isn’t your thing, Smith Rock SP is still worth visiting. It’s great for trail running, hiking, wildlife spotting, and mountain biking as well. The most rewarding (and most challenging) hike here is the 3.7-mile Misery Ridge Loop. If you’re looking for a place to camp, the park also has a walk-in area for tent camping on a first-come, first-served basis.

Smith Rock State Park is a popular attraction, and with that comes potential challenges with parking, especially during the peak season and on weekends. If you want to beat the crowds, visit on a weekday or try to get there before 8am on weekends. The parking/day-use fee costs $5.

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CLACKAMAS COUNTY

(ROUTES 3 & 5)

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TRILLIUM LAKE

Along your route from San Francisco to Portland via US-26, you’ll find the picturesque Trillium Lake sitting beautifully among the great outdoors. This lake is all about the view–featuring Mount Hood towering overhead nearby. This creates an amazing mirrored view of its snow-capped peaks, especially on a clear day.

If you have some to spare, consider doing the 1.9-mile loop hike around the lake, kayaking/paddling, fishing, or packing a picnic to enjoy here. Since motorboats are not allowed here, you’ll get an even more peaceful, enjoyable experience.

TIMBERLINE LODGE

As you approach the south side of Mount Hood, take note of the signs for the Timberline Lodge (you’ll be making a left to get there). Timberline Lodge is a magnificent historical mountain lodge, built during the Depression Era.

This is yet another great place to grab a bite to eat with a side of awe-inspiring views. The Blue Ox Bar offers pub-style cuisine, Ram’s Head Bar specializes in casual dining, and the Cascade Dining Room highlights a fine dining atmosphere.

The lodge is less than 15 minutes from Government Camp (a popular ski town) and you can expect to spend about 30 minutes to an hour here if you’re just having a peek around or grabbing some food.

If you’re looking to call it a night around here, Timberline Lodge itself is a fantastic option, boasting rustically inspired rooms that feature original handcrafted furnishings. Hotel guests can unwind after dinner with a drink at the bar or a relaxing session in the sauna or soak in the hot tub.

Fun Fact: This National Historic Landmark is perhaps most known as the exterior of the Overlook Hotel in Stanley Kubrick’s The Shining.

RAMONA FALLS

Looking for a half-day out in nature? You’re in luck then! One of the most beautiful waterfalls in the entire Northwest is just a quick hike away on your route from San Francisco to Portland–located just a 40-minute drive from Timberline Lodge (and 28 minutes from Government Camp).

The iconic 7-mile roundtrip hike on Ramona Falls Loop Trail provides stellar views of Mt. Hood and the grand Ramona Falls. The trail itself is relatively easy, but the hike requires either crossing the Sandy River on fallen logs, rock hopping, or trudging through the river.

If river crossings aren’t your thing, maybe skip this stop. It’s quite an adventure and totally worth it when you get to feast your eyes on Ramona Falls flowing down 120 feet of sheer basalt rock!

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SOUTHERN OREGON

(ROUTES 1, 2, 4 & 5)

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ASHLAND

TWE RECOMMENDED CHOICE

Because of where Ashland is located (where the Siskiyou and Cascade Mountains meet), there is no shortage of scenic views and outdoor adventure here.

While you’re here, you definitely need to take a stroll through the historic downtown and railroad district, where beautifully dated buildings now house art galleries, shops, and cafes. If you’re into theater, then you definitely cannot miss a show/production by the renowned Oregon Shakespeare Festival.

If you’d like to get more of a walk in before hopping back in the car, head straight for Lithia Park, a 90-acre park of serene, lush greenery (looking straight out of a fairytale in the fall)! This park is the absolute gem of Ashland!

Where To Stay In Ashland: Winchester Inn, Ashland Springs Hotel, or Ashland Hills Hotel & Suites

MEDFORD

TWE RECOMMENDED CHOICE

Medford is considered the heart of the Rogue Valley and is the largest city in Southern Oregon. That means there are a lot of outdoor opportunities here!

There’s the Rogue River, perfect for getting out on the water, or Upper and Lower Table Rock, two popular hiking destinations that offer nothing but epic views of the Rogue Valley and the Siskiyou Mountains.

If you don’t have the time for an entire day of outdoor adventure, you should still visit Medford! Main Street in the downtown area is lined with boutiques, antique shops, restaurants, brewpubs, and entertainment options. Definitely don’t leave without having at least one meal here!

Medford is also a great destination for families with children. Kids will love the Rogue Air Trampoline Park, Kid Time! Discovery Experience, and the nearby Rogue Valley ZipLine Adventures.

Where To Stay In Medford: Resort at Eagle Point Golf Club Lodging or Hilton Garden Inn Medford

JACKSONVILLE

Jacksonville (a National Historic Landmark) is a quaint 1850s gold rush town with a fun community vibe, located smack dab in the middle of Southern Oregon.

Here, you’ll find 100+ historic buildings lining the streets of downtown. You’ll have a lot of fun perusing the downtown area as these old buildings now house unique boutiques, restaurants, cafes, and more. For a more guided experience, take the Jacksonville Trolley Tour, which offers a 45-minute narration of the city’s past.

If you’re looking for some nature, head straight for the Jacksonville Woodland Trails. For those who love wine, venture a bit out of town for some epic wine tasting–Jacksonville marks the entrance of Applegate Valley Wine Country.

Lastly, if you absolutely love lavender, want to pick lavender, smell lavender, and/or catch these babies in full bloom, head to Lavender Fields Forever–they offer u-pick opportunities and classes (such as essential oil diffusing, wreath making, and lessons on cultivating lavender at home).

Where To Stay In Jacksonville: McCully House Inn or Wine Country Inn

OREGON VORTEX

TWE RECOMMENDED CHOICE

The Oregon Vortex located in Gold Hill, OR is an old roadside attraction from the 1930’s known for its gravity hill optical illusions & reported paranormal activity. Some backstory: John Litster, a physicist/geologist, developed the property in the 1920’s and continued to conduct experiments on the land until his death in 1959.

Many of those experiments are still featured today—apparent changes in height, objects appearing to roll uphill, and an unseen force that in some places seems to pull you off balance. It’s a whole lot of fun for the whole family and it’s no wonder— it’s arguably one of Oregon’s best-known roadside attractions.

WILDLIFE SAFARI

Wildlife Safari in Winston, Oregon is more than your average zoo—so much more. Wildlife Safari is a 600-acre “drive-thru” animal park. That’s right, you can host your own safari!

The park opened in 1972 and is the only drive-through animal park in the state of Oregon. Wildlife Safari features over 600 animals representing their wild counterparts from all around the globe. You’ll see zebra, ostrich, lions, hippos, rhinos, giraffes, bears, bison, cheetahs, tigers and so much more—all from the comfort of your own vehicle.

In terms of timing, the drive takes about 1-1.5 hours to complete.

COTTAGE GROVE

TWE RECOMMENDED CHOICE

Cottage Grove is another little Oregon town brimming with charm and cuteness. Head to the lovely downtown area to experience the best part of town. Here, you can hop out of your car and enjoy the many art galleries, shops, cafes, and boutiques.

History lovers will enjoy admiring the century-old buildings around town as well as the Bohemia Gold Mining Museum, which showcases the region’s gold-mining history.

Feeling more like outdoor activities? Cottage Grove is a great jumping-off point for activities such as hiking, biking, and horseback riding.

Where To Stay: Best Western Cottage Grove Inn

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WILLAMETTE VALLEY

(ROUTES 1, 2 & 4)

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EUGENE

TWE RECOMMENDED CHOICE

As one of the three largest cities in Oregon, Eugene has all the amenities of a big city, including public parks and trails, expansive museums, a good food scene, and a lively feel. Eugene features pretty much the best of Oregon – the ocean and the mountains are only a stone’s throw away, yet you still get the feeling of a thriving university town.

Since the city is located at the south end of Oregon’s Willamette Valley (famous for wines), you’ll find many local wine tasting options. Check out King Estate or Noble Estate for some of the best wine Oregon has to offer.

Eugene is also a fun shopping destination, especially around its downtown district. Visit the Fifth Street Public Market where you’ll find artisanal foods, local wines, and unique home and gift items. If you’re here on a Saturday, don’t miss the Eugene Saturday Market, which runs from April through mid-November.

Where To Stay In Eugene: EVEN Hotel Eugene, an IHG Hotel

SILVER FALLS STATE PARK

TWE RECOMMENDED CHOICE

Famous for its abundance of picturesque waterfalls, Silver Falls State Park is the largest and one of the most popular state parks in Oregon. Located 60 miles south of Portland in the foothills of the Cascade Mountains, Silver Falls SP features some truly iconic hikes and sights. It is best known for the 177-foot South Falls, located at the South Falls Day Use Area.

If you have more time to linger here, you should really make time to hike the epic Trail of Ten Falls, a moderate 7.8-mile hike that features ten waterfalls. This trail allows visitors to walk directly behind four different waterfalls, providing you with an awesome perspective and an even more awesome photo op!

The hike will take approximately 3 hours to complete and is suitable for families and beginner hikers as there are side trails you could take to shortcut it back to your car.

You can also stop by the historic South Falls Lodge where you can pick up sandwiches, snacks, coffee and ice cream before/after your hike. There is also a nature store there for souvenir shopping.

SALEM

Salem, the capital city of Oregon, is located in the center of the Willamette Valley, 47 miles from Portland. Salem is known for its scenic beauty, as you’ll immediately notice once you step out of your car. You’ll be surrounded by gardens, flower fields, vineyards, and green pastures!

Try some award-winning cheeses at Willamette Valley Cheese Company, sample wines from various wineries in the region, or enjoy a riverboat Sunday brunch on the Willamette Queen.

Where To Stay In Salem: Home2 Suites By Hilton Salem or Residence Inn Salem

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MULTNOMAH COUNTY

(ROUTES 3 & 5)

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COLUMBIA RIVER GORGE

TWE RECOMMENDED CHOICE

The Columbia River Gorge is so beautiful and packed with jaw-dropping waterfalls, overlooks, and hikes that they named it a National Scenic Area. The Historic Columbia River Highway Scenic Byway is actually considered one of the most scenic drives in the country.

Along this 70-mile highway, you will have the chance to see several historic buildings, monuments, fish hatcheries, the Oneonta Gorge, and numerous waterfalls including Latourell Falls, Multnomah Falls, Wahkeena Falls, Shepperd’s Dell Falls, Bridal Veil Falls, Wahclella Falls, and Fairy Falls.

Even if you don’t decide to take routes #3 or #5, you should still make time to explore the Gorge while you’re in the Portland area–it’s drop-dead gorge-eous. And best of all, it’s less than an hour away from Downtown Portland!

Because this area is jam-packed with fun stuff to do, we dedicated an entire post to outline everything! Check out our Columbia River Gorge day trip guide here to learn more about what to see and do.

Note: Given recent fires over the years, it’s best to check their website to check for trail closures.

Don’t want to plan out your Columbia River Gorge route? Consider one of these day trips/excursions (from Portland) so you can enjoy epic views of the Columbia River Gorge without having to worry about any of the logistics:

• Columbia River Gorge Bike & Hike Tour – Bike and trek through the magnificent Columbia River Gorge on this half-day trip from Portland. You’ll get to bike through the Gorge and stop to hike and explore majestic waterfalls. Highly recommend this one!

• 30-minute Multnomah Falls & Columbia Gorge Air Tour – An airplane ride to see the famous Multnomah Falls with beautiful aerial views? How epic is that!

• Morning Half-Day Multnomah Falls and Columbia River Gorge Waterfalls Tour from Portland – stops at the magnificent falls of Multnomah, Latourell, and Bridal Veil

PORTLAND

Portland is a vibrant, bustling city in Oregon and is one of the greenest cities in the world. Portland prides itself on embracing culture, creativity, progressiveness, and weirdness, which makes this city so fun to explore. There are tons of quirky neighborhoods to explore, each with its own unique atmosphere and personality.

Take a walk through a few of them and you’ll find yourself in a world of microbreweries, apothecaries, independently owned bookstores, vintage shops, vegan restaurants, artisanal coffee shops, and dazzling murals.

The food truck scene is popping, as are the coffee and craft beer scenes. What more could you ask for? Could your belly be in a happier place?

If you’re starting (or ending) your road trip in Portland, make sure you have at least three extra days to eat, drink, and explore the city of Portland!

Want more on Portland? Here are some more helpful posts: 

• 35+ Affordable, Unique, and Off The Beaten Path Things To Do in Portland
• The Perfect Day Trip From Portland to The Oregon Coast
• The Best Neighborhoods To Visit In Portland, Oregon

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Starting your trip from Portland and can’t get enough of the road-tripping goodness? Consider extending your trip from SF to Los Angeles. Why not read our guide on the best stops from SF to LA!

Read More:

9 Epic Weekend Road Trips From Portland, Oregon To Take This Year

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San Francisco to Mendocino Road Trip: My Summer Road Trip Experience (Part 1)

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15 Fun-Filled Road Trips From Seattle, Washington