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

Portland is amazing in itself, with so many unique eating, drinking, hiking, and cultural activities to busy yourself with. But from time to time, you may find yourself just itching to get away and explore what lies beyond the city limits.

You’re in luck, because Portland is the perfect launching point for a weekend road trip! With the city being so centrally located in the Pacific Northwest, your opportunity for a new adventure grows tenfold!

Taking a road trip from Portland, Oregon means you’ll get to explore the coast, mountains, deserts, forests, and even nearby metropolitan cities like Seattle.

Not only are these destinations amazing in themselves, but the journey getting there will be equally enjoyable, especially when passing through iconic roads like the Historic Columbia River Highway or any of Oregon’s scenic byways.

Read on to discover the 9 best road trips from Portland that you can take over the course of a weekend or even a week-long adventure! You’ll easily see why everyone who visits the PNW falls immediately and completely in love with it.

*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!


The best time to take a road trip from Portland depends entirely on what you want to do, see, and experience.

If you’re looking to spend more of your time outdoors in the warm sunny weather, travel during the summer or fall seasons. If you’re looking to do some serious snowboarding, the mountains are best in the winter season.

The coast is more popular during the summer, but if you’re interested in witnessing the epic winter storms seen here, you might want to take your road trip to the coast in the winter season.

Though the weather changes pretty drastically in the PNW (summers bring sunshine and perfect hiking weather while winters bring snow and frozen waterfalls), the road trips listed below remain open and accessible all year round.


If you don’t have a car or don’t have a reliable car you trust to get you out of Portland and back in one piece, I suggest you pick up a rental car for your road trip.

If you are the type to compare prices between rental car companies like us, use Rentalcars.com to search for the best option. Not only does the tool allow you to compare rental car prices, but most of the time you can book with no prepayment and no cancellation fees.

Mendocino to Redwood National Park Road Trip

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.

Don’t Forget About The Pass!

A lot of the best adventures around Oregon will require a day-use fee. The better deal? Get yourself a Northwest Pass or an Interagency Annual Pass. You can easily get one delivered straight to your door. Order one before your trip!


If you’re a planner like me, you’re probably going to want to book all your lodging before you leave. I don’t know about you, but the thought of not having a place to stay (or paying an arm and a leg to get a room last-minute) just makes me uneasy.

Be sure to book your lodging before you leave, or as soon as possible really, especially if you’re planning on staying at a specific hotel or yurt that you’ve been eyeing for some time.

Planning your Oregon road trip in advance? Save on travel costs by booking your accommodations through this platform! Their ‘no prepayment’ and ‘free cancellation’ features are unbeatable.


Right before your trip, check Google Maps or TripCheck (by the Oregon Department of Transportation) before you hit the road.

We actually like TripCheck a little bit more for this exercise, because not only does it provide you with live road condition information, but it also gives you live weather alerts as well!

There are even live cameras you can check out to see exactly how snowy a mountain pass may be or how bad the traffic is in the city. Though not as detailed as within Oregon, the highway condition information even extends to nearby states!

If you’re traveling in the wintertime, make sure to pay closer attention to road conditions. Road closures tend to be more common in the wintertime.


License and registration | This is a no-brainer, but always good to check you have all documents before it’s too late and you get too far away from home. Do NOT leave home without them. They are road trip essentials!

Spare Tire | In addition to carrying a spare tire with you, don’t forget to check your current tire conditions before you set off as well.

Jumper Cables / Car Jump Starter | A must-have for any road trip! If you’re looking to invest in something exponentially more powerful/convenient than simple jumper cables, get the NOCO Boost HD Car Battery Jump Starter Box. This tool was sent from heaven and serves as a car jump starter, portable power bank, LED flashlight, and 12-volt portable power–all in one!

iOttie car mount | This is my partner in crime on any road trip. It’s got an amazing grip and popping your phone in and out of the mount could not be easier. If you’re renting a rental car and you’re not sure if it has a navigation screen, bring a phone mount with you. The iOttie attaches by suction, so it’s easy to transport from car to car.

Roadside Emergency Kit | You never know what kind of car trouble you may encounter on the road. This convenient little kit contains 42 roadside emergency components, including jumper cables, an aluminum flashlight and batteries, 2-in-1 screwdriver, duct tape, poncho, cable ties, bandages, towelettes, and zipper-lock bags.

Trunk Organizer | With any road trip comes lots and lots of stuff to pack. Keep your road trip essentials organized with a trunk organizer. Not only will this make it so much easier to find what you need, but it will also lead to more space in your trunk for you to pack other necessities.

Portable Cooler | Coolers are a must for any road trip. Not only will you be able to keep beverages cold and refreshing, but you will also be able to keep perishables fresh. A portable hard cooler will allow you to pack picnic lunches, bring cheese and jams, and more.

Redwood National Park Road Trip


Alright now that we’ve gotten all the logistics out of the way, let’s get into the meat of it! Below are the 9 best road trips from Portland, perfect for long weekend adventures or even week-long journeys throughout the state.


Distance from Portland: 60 miles to Hood River (approximately 1 hour driving time)

columbia river gorge sunset

You didn’t think we could have a Portland road trip list without the Columbia River Gorge, did you? This is one of the most iconic and easiest-to-access road trips from Portland and can be done as a day trip or a weekend road trip.

The Columbia River Gorge is so beautiful and packed with jaw-dropping waterfalls, overlooks, and hikes that they designated it a National Scenic Area. On top of that, 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 charming towns, historic buildings, monuments, fish hatcheries, and countless numbers of enchanting waterfalls. Not to mention, the hiking and watersports possibilities are endless.

On your way to the Columbia River Gorge, stop by the historic property of McMenamins Edgefield for lunch, right before embarking on a full-day adventure in the waterfall area of the CRG. Be sure to make a stop at Multnomah Falls because it’s a must-see as you travel along the Historic Columbia River Highway Scenic Byway.

From there, pay the nearby towns of The Dalles and Cascade Locks a visit, offering a variety of activities for craft beer lovers, foodies, cyclists, day hikers, and nature lovers.

Lastly, take some time to explore Hood River, an idyllic town at the foot of Mount Hood. It’s an outdoor-lovers paradise with various mountain excursion opportunities as well as river-related recreational activities. Windsurfing is a super popular activity here, so why not try some windsurfing lessons while you’re here?

Check out our roundup of the best things to do on a Columbia River Gorge road trip from Portland.

Suggested Duration: 1-2 days

Where To Stay: A great place to call your turnaround point is Hood River, OR. Our favorite stylish hotels in the Hood River area include Hood River Hotel (the oldest hotel in Hood River, yet extremely modern) and RubyJune Inn (located on the Washington side of the Columbia River, just 10 minutes drive from Hood River).


Distance from Portland: 95 miles (approximately 2 hours driving time)

17 Unique Things To Do In Cannon Beach Oregon - Travels With Elle

Fancy a short weekend trip out west to the Oregon Coast? This road trip features three towns filled to the brim with things to do: Astoria, Seaside, and Cannon Beach. Set out from Portland to Astoria and work your way southbound.

Be sure to try a few breweries in Astoria, explore the family-friendly town of Seaside and have yourself a picnic at Haystack Rock in Cannon Beach. If you love hiking, you absolutely can’t miss the opportunity to explore Ecola State Park and Fort Stevens State Park.

For more details on what to do on this Oregon Coast road trip, check out this Northern Oregon Coast road trip we took last summer, featuring Astoria, Seaside, and Cannon Beach!

Though we completed this trip in one day, I recommend spending a night or two there to fully take in the sights, sounds, and amazing food the Oregon Coast has to offer. There’s so much nature to explore on the coast, you’ll really be doing yourself a favor by staying longer and giving this area the time and attention it deserves.

Looking to lengthen the trip or explore additional towns? Add Tillamook, OR to your itinerary (yes, the cheese was named after this town), or head further south along the coast to Newport, Devils Punchbowl State Park, and Oregon Dunes National Recreation Area.

Suggested Duration: 2-3 days

Where To Stay: Our top recommendations are the Ashore Hotel Seaside and the Selina Commodore Astoria.


Distance from Portland: 60 miles (approximately 1.5 hours driving time)

mount hood oregon - Best Road Trips From Portland, OR - TravelsWithElle

Mount Hood is probably one of the more popular road trips from Portland in the winter season. Mount Hood, visible from Portland on a clear day, is a premier destination for travelers looking to spend some time outdoors.

It also boasts the longest ski season in North America, with lifts operating year-round, so it’s no wonder it’s one of the top Portland road trips for skiers and snowboarders.

Despite its popularity among people who enjoy snowsports, Mount Hood makes for a wonderful summer/fall road trip destination as well. During the warmer seasons, the primary draw is Mount Hood’s wonderful hiking trails.

On this road trip from Portland, you’ll pass by favorite destinations such as the Columbia River Gorge and Hood River. Drive a bit further and you’ll reach the Mount Hood area in no time. After hiking or engaging in snowsports (whatever your poison is), take time to explore the surrounding area of Mount Hood, because there’s a lot to see and do.

On the south side of Mount Hood sits the Timberline Lodge, an iconic historic hotel that was built during the Depression Era. This is a great place to grab a bite to eat with a side of awe-inspiring views. Fun fact for you–this National Historic Landmark is perhaps most known as the exterior of the Overlook Hotel in Stanley Kubrick’s The Shining.

From there, head to Government Camp’s Skibowl where you’ll find the Mount Hood Adventure Park. This is an awesome spot for families to enjoy the alpine slide, disc golf, mountain biking, batting cages, and more. “Govey,” as the locals call it, is a quaint alpine village that has plenty of eateries, watering holes, and an abundance of small-town charm.

And just 10 minutes south of Government Camp, you’ll find the picturesque Trillium Lake sitting beautifully among the great outdoors. This lake is all about the view and is often considered a must-see near Mount Hood.

trillium lake oregon - Best Road Trips From Portland, OR - TravelsWithElle

Suggested Duration: 1-2 days

Where To Stay: Without a doubt, the most memorable place to stay around Mount Hood is the Timberline Lodge. The historic atmosphere (and delicious food served at the restaurant) is something you need to experience for yourself. Another option is the Whispering Woods Resort, located in Welches near Mt Hood Village, situated near popular restaurants and activities in town.


Distance from Portland: 230-250 miles (approximately 5 hours driving time)

Crater Lake National Park - Travels With Elle

If you’ve got a long weekend or even a week to spare, a road trip from Portland to Crater Lake National Park, Oregon should be on your must-do list. The normal drive from Portland to Crater Lake National Park can easily be tackled in 4-5 hours.

But you wouldn’t want to make that drive without stopping to see some of the awesome spots, hikes, and sights in between, right? That’s right! Because the drive from Portland to Crater Lake National Park is drop-dead gorgeous.

Don’t miss iconic spots along the way including the Columbia River Gorge, Ramona Falls, the city of Bend, Mount Hood, Smith Rock State Park, Newberry Crater, Lava River Cave, and much more.

Be sure to spend a few days in the outdoor paradise of Bend, OR before continuing on to Crater Lake National Park. As you can see, there are way too many exciting activities to do along this route to fit it all in just a short weekend.

To help you make the most of your trip, we’re sharing a complete list of our favorite stops to explore along the way on a road trip from Portland to Crater Lake National Park.

Suggested Duration: 4 to 7 days

Where To Stay: Our top recommendations along this route include the Timberline Lodge in Mount Hood and LOGE Bend, Riverhouse on the Deschutes, and Pine Ridge Inn in Bend, OR.


Distance from Portland: 138 miles (approximately 2.5 to 3 hours driving time)

18 Best Things To Do At Mount Rainier National Park For First Timers - Skyline Trail

Mount Rainier National Park holds a spot very near and dear to my heart as well as for many other adventure travelers. It’s a mountain lover’s paradise! This national park is massive and with that comes a lot of territory waiting to be explored! It’s no wonder this is one of the most popular Portland road trips.

First-time visitors to Mount Rainier NP should prioritize a visit to the Paradise Valley area, followed by the Sunrise area. These areas offer very different experiences from each other, but both offer stellar views of Mount Rainier in all its glory.

There are a ton of epic hiking trails to explore, as well as a ton of beautiful waterfalls to ogle at! Be sure to make time to eat at Wildberry Restaurant in Ashford, WA, a local Nepalese restaurant that serves up one of the best burgers we’ve ever had in our lives–the Summit Burger.

Read more about what to see, do, and eat on our Portland to Mount Rainier National Park road trip!

Pro Tip: Don’t forget to buy or bring your America The Beautiful National Parks Pass! If you plan on visiting a few other national parks within a year’s time, I recommend you get this pass, which costs $80. As long as you visit 2 additional national parks, the pass will more than pay for itself and save you so much money on park admission fees.

Suggested Duration: 2-3 days

Where To Stay: The two main towns that offer lodging and accommodation are Packwood, WA and Ashford, WA. Options are a bit more limited here compared to other destinations, but we recommend Packwood Lodge in Packwood or the historic Alexander’s Lodge in Ashford.


Distance from Portland: 162 miles (approximately 3 to 3.5 hours driving time)

Deschutes River Trail - Things to Do in Bend, Oregon - Travels With Elle

We hear a lot about how it’s not about the destination, but more about the journey it takes to get there. While we are firm believers in that statement, in the case of Bend, Oregon, it’s equally about the destination as it is about the journey!

Bend is an absolute haven for outdoor enthusiasts and you have to do it justice by allocating a few days of exploration just in this city alone.

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. If you have extra time, don’t miss the nearby towns of Redmond, OR and Sisters, OR.

On your road trip to Bend, you will pass by various types of scenery, starting with the densely forested atmosphere of the Portland area all the way to the high desert flora and fauna of Central Oregon.

To help you make the most of your trip, we’re sharing a complete list of our favorite stops to explore along the route from Portland to Bend, OR.

And when you get to Bend itself, oh boy are you in for a treat. There are so many things to do in Bend alone, such as visiting all the breweries, lounging on the river, or chasing all the waterfalls nearby!

Suggested Duration: 3-5 days

Where To Stay: We love staying in Bend whenever we get the chance! Our top recommendations include LOGE Bend, Riverhouse on the Deschutes, and Pine Ridge Inn.


Distance from Portland: 118 miles (approximately 2 hours driving time)

When you opt for a road trip from Portland to Eugene, you’re going to be getting a pretty mixed bag of culture and adventure. I’d recommend taking Highway 99W south from Portland. This way, you’ll pass right through the heart of the Willamette Valley. The Willamette Valley is particularly known for having wonderful wine, craft beer, and great food.

Between Portland and Eugene, you’ll hit Corvallis, which is a great spot in the microbrew scene. Another cool spot to hit up is the Evergreen Air & Space Museum, showcasing the history of air travel and space flight. It’s also home to lots of historic aircraft.

If you’re a hiking enthusiast, Silver Falls State Park is a no-brainer. This is one of the most famous hikes in Oregon, as you’ll get to walk over, under, and even behind 10 waterfalls on the Trail of Ten Falls.

Once you reach Eugene, OR, you’ll need to unpack your bags at a hotel and get to exploring! 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 (plus a youthful nightlife crowd too).

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.

If you’re interested in the region’s history, consider visiting the Applegate Pioneer Museum or Bohemia Gold Mining Museum.

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.

Got more time? Why not head west from Eugene toward the Central Oregon Coast? If you’re in the mood for small towns, coastal views, good seafood, and a whole lot of sea lions, this road trip is for you!

Suggested Duration: 3-5 days

Where To Stay: Eugene is home to a boatload of modern, stylish, and affordable hotels. We recommend Graduate Eugene and The Gordon Hotel, both equally as hip as the other. We also love Inn at the 5th for a more luxury stay (the rooms are immaculate).

The Graduate Eugene - Where To Stay In Eugene Oregon
I love Graduate Eugene for all my trips into town!


Distance from Portland: 175 miles (approximately 3 hours driving time)

Portland To Seattle - Best Road Trips From Portland, OR - TravelsWithElle

Seattle is a vibrant city that offers a wide array of indoor experiences and outdoor escapes. In Seattle, there’s of course the Chihuly Garden and Glass Museum, Kerry Park, The Space Needle, and Pike Place Market.

And that barely scratches the surface. The options for how to spend a weekend in this bustling city are nearly endless!

The distance from Seattle to Portland is approximately 180 miles and only takes about three hours if you stick to the I-5 freeway and don’t make any stops. But within that 180-mile stretch, there are many cool spots worth checking out, and even more if you’re willing to venture a little further off the main highway.

On the way to Mount St. Helens in Washington is the 3,000-acre Silver Lake, where visitors can find nearby trails, camping, fishing and boating. And then there’s Mount St. Helens herself, where you can learn more about the famous volcano in Castle Rock, WA at the different visitor centers.

If you have a few extra days to spare, stop by Mount Rainier National Park to witness the majestic glacier-capped mountain for yourself. Or any of these many beautiful places that call Washington home!

Before heading into Seattle, stop by Point Defiance Park, a sprawling urban park that includes a zoo and aquarium, Fort Nisqually Living History Museum, breathtaking flower gardens, as well as beaches and trails.

If you have the time, a few other spots to consider including in your Seattle to Portland road trip itinerary include Lewis and Clark State Park, Bachelor Island, Longview, WA, and Westport, OR. Looking to explore a little further out from Seattle? Take a day trip over to Olympic National Park.

Road tripping with your significant other? Seattle’s got a ton of awesome spots perfect for date nights too!

Suggested Duration: 3-4 days

Where To Stay: For style, comfort, and proximity to the city center, we like Inn at the Market and The Paramount Hotel. For a stay closer to The Space Needle, we like The Mediterranean Inn.


Distance from Portland: 200 to 275 miles (approximately 4 to 5 hours driving time)

John Day Fossil Beds National Monument - Best Road Trips From Portland - Travels With Elle

The large and expanse region that makes up John Day Fossil Beds National Monument is best described as otherworldly. Just 1.5 hours from Bend and quietly tucked away in Eastern Oregon, is the John Day Fossil Beds.

This area is so impressive that it’s made it onto the 7 Wonders of Oregon list! As soon as you catch your first glance at the painted hills, craggy rock formations, and breathtaking peaks, you’ll immediately see why!

This area of the state is known for its incredibly preserved layers of fossil plants/mammals that lived in the region from about 45 million years ago to 5 million years ago.

The monument is broken down into three units–the Sheep Rock Unit, Painted Hills Unit, and Clarno Unit (most remote). Sheep Rock Unit features a mesmerizing canyon drive and fossil museum, while the Painted Hills Unit features unforgettable hikes through multi-colored rock formations.

There are two main routes to get to John Day–one that takes you through the Columbia River Gorge and another that bypasses the Mount Hood area. Pick the route that you want to explore more (the mileage difference between the two routes is only 30 miles).

Once you get to the mouth of the John Day Fossil Beds National Monument, spend your first night near the Painted Hills Unit so that you can explore the area bright and early the following day. You can easily spend half a day exploring in this area alone.

From there, hop back into your car and make your way to the Sheep Rock Unit.

Break your nature sightseeing up by heading to the nearby villages of Prairie City, OR (30 minutes from the Sheep Rock Unit) and Fossil, OR (30 minutes from the Clarno Unit / 1 hour from the Painted Hills Unit). You’ll find plenty of local restaurants, small museums, and even quirky activities like fossil hunting to round out your weekend adventure.

Suggested Duration: 3-4 days

Where To Stay: Country Inn & Suites by Radisson, Prineville, OR – hotel options are extremely limited in this area, but Prineville is the town that has the most amenities (it is located about an hour away from the Painted Hills).

And there you have it, some of the best weekend road trips from Portland, Oregon! We hope you were able to discover something new to fuel your next road trip! Wishing you safe and happy travels.

Read More:

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Trail Of Ten Falls: How To Hike This Epic Trail

The Perfect Central Oregon Coast Road Trip: 8 Fun Stops To Make

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Elle Leung

My name is Elle and I'm a travel blogger and adventurer based in California. I love helping people plan trips and create unique itineraries based on their interests and their budgets. I'm a huge fan of outdoor adventures and doing off-the-beaten-path things in my state (and all around the world too)!

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