Oregon is arguably the most picturesque state in America, and the best way to explore its diverse landscapes is a thrilling road trip from Portland. The moment you hop in the car, the scenery outside your window takes your breath away with their unspeakable beauty. From the rugged Oregon Coast to the snow-capped peaks of the Cascades, you could spend a lifetime marvelling at Oregon’s natural wonders.

So, how much of this beautiful state can you explore in 10 days? Unfortunately, that’s nowhere near the amount of time needed to fully appreciate Oregon’s natural beauty. But that’s why I’ve picked out my absolute favourite places to give you an itinerary jam-packed with adventures. Trying to find the right balance of driving time and number of places to visit each day is an excruciating task while road tripping through Oregon.

My itinerary also gives you the chance to visit some of Oregon’s friendly small towns nestled in the countryside. From the joyful communities of the Willamette Valley to the recreational haven of Bend, you’ll see why Oregonians take so much pride in their state. There are also some tips on which are the best areas to delve into Oregon’s sprawling wine and craft beer scenes.

Oregon ranks high on my list of favourite American states, and road-tripping from Portland is an incredible way to see it. I loved every minute of this itinerary and hope you enjoy it as well!

Portland Road Trip – 10 Days

Portland to the Oregon Coast | Oregon Coast to Willamette Valley | Smith Rock State Park | Crater Lake National Park | Bend | Painted Hills | Mount Hood National Forest | Hood River | Columbia River Gorge | Multnomah Falls & Depart Portland | Places for Next Time |

Day 1 – Portland to the Oregon Coast

Before hitting the open road to the Oregon Coast, let’s make one beautiful pit stop before leaving the “City of Roses.” The International Rose Test Garden sits only a few miles outside of downtown Portland, and the colourful varieties from its 10,000+ rose bushes earned the city its catchy moniker. You’ll find the rose garden inside Washington Park and perched upon a hillside with gorgeous views of Portland and Mount Hood.

Now it’s onward to the Oregon Coast!

Our itinerary won’t cover the entire 363-mile stretch of Oregon’s west coast, but I’ve added many of its most picturesque locations. The first stop is Cannon Beach to marvel at Haystack Rock towering over its shores. Standing at 235 feet tall, it’s believed to be one of the world’s tallest intertidal monuments. Make a short drive over to Hug Point to explore its mysterious sea caves or venture to Ecola State Park for unbelievable vistas of the rugged coast.

Drive southwards towards Tillamook Bay to connect to the Three Capes Scenic Loop. This 40-mile route shows off the Oregon Coast in its purest splendour and will take your breath away. The panoramic views of the sandy shores, rocky headlands, and old-growth forests give you countless photo opportunities. Three sights on the loop that are a must-see include Cape Meares, Cape Lookout, and Cape Kiwanda.

Day 2 – Oregon Coast to Willamette Valley

Before veering off Hwy 101 to explore the scenery of central and eastern Oregon, I saved one more stop on the Oregon Coast. About 1-hour from Tillamook Bay, Neskowin Beach features two of the more bizarre sights of the coastline.

One thing you’ll notice on the Neskowin shores are the stumps protruding from the sand. It’s actually the remains of a coastal forest that once had trees standing nearly 200 feet tall. The remnants of these trees didn’t surface until the end of the 20^th century when a storm ravaged the Oregon coast. Just off the coast, the gigantic Proposal Rock has a romantic story about a lovestruck sea captain, and you’ll find various marine creatures at low tide.

Turn onto Oregon Route 18 and then towards Oregon Route 22 to head inland towards Salem, the Oregon state capital. Situated in the heart of the Willamette Valley, Salem boasts a dynamic scene of outdoor activities, cultural attractions, and renowned wineries. The surrounding area includes dozens of wineries where you can taste the Pinot Noir that the region is famous for.

For nature lovers, the Willamette Valley holds the crown jewel of the Oregon State Park System. Only a 30-minute drive from Salem, Silver Falls State Park is an enchanting location to chase waterfalls. The star attraction of the park is the Trail of Ten Falls, a 7.6-mile loop that meanders through old-growth forest to 10 stunning cascades.

After sipping wine or standing behind waterfalls, spend the night in one of the many charming towns dotting the Willamette Valley. Mt. Angel and Silverton are two delightful options less than 30 minutes outside of Salem.

Day 3 – Smith Rock State Park

The versatility of Oregon’s natural scenery shines as you drive towards another incredible state park. Known as the birthplace of American sport climbing, Smith Rock State Park attracts rock climbers from all over the world. Sitting in the high desert of central Oregon, the park is awe-inducing its craggy spires and sharp canyons dotting the landscape.

Get an early start from your accommodation since the drive from Salem to Smith Rock is roughly two and a half hours. Once you reach Smith Rock, you have endless recreational activities at your fingertips. Take your choice from thousands of climbing routes, tackle hiking trails for views of the high desert, or spot an enormous amount of wildlife.

Misery Ridge Trail challenges trekkers with a climb to a 3,360-foot summit with jaw-dropping views of the rocky cathedrals. For seasoned rock climbers, Monkey Face is the park’s iconic symbol for its unique shape and variety of paths to the top. To appreciate the beauty of the high desert, go horseback riding or float along the Crooked River.

The nearby town of Redmond has lots of accommodation options, and there are campgrounds at Smith Rock State Park if you brought camping gear. First-come, first-served camping is available at the Bivy Campground and Skull Hollow Campground is eight miles from the park.

Day 4 – Crater Lake National Park

Wake up early for another full day discovering one of Oregon’s natural wonders. From Smith Rock State Park, take Hwy 97-South towards the beautiful town of Bend, through Deschutes National Forest and onwards to Crater Lake National Park. With the amount of stunning natural beauty across Oregon, it’s hard to believe that Crater Lake is the only official national park in the state.

The 2-hour drive to Crater Lake alone weaves through the Cascade Range and treats you to spectacular views of many towering peaks. Mount Hood lies farther to the north and is Oregon’s tallest peak, but you should be able to spot the next highest peaks today. Catch a view of Mount Jefferson from Smith Rock before you leave, find South Sister and its shorter siblings, and gaze at the jagged peak of Mount Thielsen right before you reach Crater Lake. Other Cascade peaks you’ll see on a sunny day include Mount Bachelor, Mount Scott, and Diamond Peak.

Don’t leave the car quite yet when you reach Crater Lake. Measuring 33 miles around the deep sapphire-blue lake, the Rim Drive gives you dramatic vistas of the slumbering volcano. Evergreen forests and snowy peaks decorate the backdrop as you peer into the depths of America’s deepest lake.

Stretch your legs by tackling the hiking trails that give you a closer look into the volcano that blew its top thousands of years ago. Starting from the parking lot of the Crater Lake Lodge, the 3.4-mile Garfield Peak Trail makes a steep climb to the ridge overlooking the lake. The Cleetwood Cove Trail descends to the shoreline and offers the chance to catch a scenic boat ride to Wizard Island, the mysterious cinder cone inside the crater.

Day 5 – Bend

Next head back towards Bend for an opportunity to drive the Cascade Lakes National Scenic Byway. From Crater Lake National Park, veer off Hwy 97 and onto Oregon Route 58 (also called Willamette Highway) before turning onto the Cascade Lakes Scenic Byway. The 66-mile roadway meanders through the Cascade Range and the Deschutes wilderness before ending in Bend.

Along the way, you’ll gain stellar views of the snowy peaks and drive past several sparkling lakes. Each of the Cascade lakes is a hub for recreational activities and those enjoying the tranquillity of Deschutes National Forest. Summer creates the perfect time for Bend residents to go on lakeside vacations for hiking, boating, kayaking fishing, biking, camping, or simply admiring the majesty of the Cascade Range. Some of the breathtaking lakes on the byway to make a pit stop include Todd Lake, Elk Lake, Lava Lake, Devils Lake, and Sparks Lake.

Once you reach Bend, kick your feet up for the evening and sample some of the finest microbrews in town. Visitors to Oregon may think Portland is the beer mecca, but don’t sleep on Bend and its 20+ breweries. In the past decade, Bend has even earned accolades as one of America’s best beer cities. Some of the must-see brewpubs in the area include Bend Brewing Company, Deschutes Brewery Bend Public House, and 10 Barrel Brewing West Side Bend. If you want to spend a few extra days in Bend here are some other fun things to do in Bend.

Day 6 – Painted Hills

After a night of tasty brews and pub fare, it’s time to hit the road again for another one of Oregon’s natural beauties. The scenery takes another crazy turn as we continue northeast towards the Painted Hills. Part of the John Day Fossil Beds National Monument, this geologic wonder looks like an image taken from a nature lover’s wildest dream.

Just outside of Mitchell, the John Day Fossil Beds are roughly 85 miles from Bend a straight shot once you hit Hwy 26-East. Hiking around the colourful hills lets you admire the craftsmanship of Mother Nature. The landscape here is a result of climate change that started millions of years ago. Once a fertile river floodplain, distinct soils produced a wide variety of colours as a more tropical climate took shape. Prehistoric species roamed the area, and their fossils give scientists a clue to the Earth’s history.

The layered bands produce vibrant hues of red, orange, yellow, black, and grey that offer unique images throughout the day. Sunlight and moisture alter the colours, and each season presents the Painted Hills in a different light. If your Oregon road trip is during spring, wildflowers often engulf the area around the hills.

Don’t forget to check out the two other areas of the John Day Fossil Beds during your visit. The Clarno Unit features craggy cliffs that formed over 40 million years ago and reveal striking fossils of the animals that once lived in the lush jungle here. Sheep Rock is an impressive landmark displaying layers of volcanic ash reshaped from ages of climate change.

Day 7 – Mount Hood National Forest

Get back on Hwy 26-West and drive back towards the Cascades for the next adventure on this Oregon itinerary. The journey from the Mitchell area to Mount Hood National Forest takes nearly three hours with no stops, but we’re spending the next two days exploring the Mount Hood wilderness.

With Oregon’s tallest peak overlooking the landscape, the pristine forest here is packed with exciting outdoor and cultural activities. The first stop today is Trillium Lake for a flawless panorama of Mount Hood. Sitting directly beneath the snowy peak, the Trillium Lake Campground is a popular place for Portlanders to get away for the weekend. The Trillium Lake Loop circles the lake, its boat ramp is a launching pad for kayakers, and the fishing pier draws anglers searching for trout.

For hikers, the nearby Tom Dick and Harry Mountain Trail starts a few miles from Trillium Lake. The 9-mile trail gets your blood flowing, leads to the picturesque Mirror Lake, and offers magnificent views of Mount Hood.

There’s a wide range of accommodation options within the forest due to its close distance to Portland, and you shouldn’t have any problems finding a room. Your options include resorts, cabins, lodges, and campgrounds. To immerse yourself in one of Oregon’s historic pieces of architecture, consider staying at the Timberline Lodge and Ski Area. Constructed by local artisans at the height of the Great Depression, the famous mountain lodge made an appearance in Stanley Kubrick’s The Shining.

Day 8 – Hood River

So far, we’ve only had time to explore one side of this majestic mountain. The Mount Hood Scenic Byway stretches 105 miles around the stratovolcano for some of Oregon’s most dramatic scenery. Although the drive begins close to Portland, we’re going to start farther along the byway.

When you reach Hwy 26, turn onto Oregon Route 35 near Government Camp. The alpine village is a recreational and cultural hub and worth exploring if you have time to spare. Hikers, skiers, mountaineers, and other thrill-seekers use the community as a base to reach the south slope of Mount Hood. You’ll also find the Mount Hood Cultural Center and Museum where you can learn about the history of the region.

The drive along Oregon Route 35 doesn’t take long, but a stop at the Tamanawas Falls Trailhead lets you take a 3.3-mile hike to an enchanting waterfall. Cruising through the Hood River Valley, you’ll have the chance to veer onto the Hood River Fruit Loop if you wish. The route serves as a gateway to the fertile soils of the valley that give farmers and vintners perfect conditions to grow fresh crops throughout the year. Fruit stands, farms, vineyards, and flower gardens decorate the landscape, and there’s always something in season for you to taste.

Hood River marks the end of today’s journey, and this charming town sits at the confluence of the Hood and Columbia rivers. Downtown Hood River entertains visitors with fabulous restaurants, boutique shops, and a laid-back vibe. If you’re still up for adventure, Hood River is a goldmine for kayakers, paddlers, and windsurfers. In fact, the town is considered the windsurfing capital of the world due to the fierce winds shooting from the Columbia River Gorge.

Day 9 – Columbia River Gorge

The final full-day of this Oregon road trip starts to make the detour back to Portland but saves one of the state’s most treasured places for last. From Hood River to The Dalles, travel down every driveable stretch of the Historic Columbia River Highway. Although parts of the scenic roadway are no longer accessible by car, the 74-mile journey gives you jaw-dropping views of the Columbia River Gorge.

Known as the “King of Roads,” the route became America’s first planned scenic roadway and was immensely popular from the 1920s to 1950s. The construction of I-84 led to the neglect or destruction of several sections of the iconic two-lane road. However, there has been much effort in recent years to restore as much of the old highway as possible. Drivers, cyclists, and hikers all have access to sections of the route that show off the majesty of the gorge.

A driving tour along the Columbia River Gorge puts you on the doorstep of cascading waterfalls, lush forest, and mossy canyons. You’ll likely stop every few minutes for pictures of dramatic vistas or explore enchanting hikes for a closer glimpse of the Columbia River. The roadway itself is a decorated part of Oregon’s history for its elegant bridges and excellent stonework.

Many of the spectacular viewpoints of the Columbia River Gorge dot the highway and provide unbelievable photo opportunities. The Portland Women’s Forum State Scenic Viewpoint, Crown Point State Scenic Corridor, and Bridal Veil Falls State Scenic Viewpoint are three of the best to stop.

Day 10 – Multnomah Falls & Depart Portland

The final day of your itinerary is dedicated to arguably Oregon’s most famous tourist attraction, Multnomah Falls. Standing at 620 feet tall, the two-tiered cascade gracefully tumbles through the gorge and draws millions of visitors each year. To beat the crowds, I’d recommend getting an early start to the day to ensure you get a parking spot. On weekends and during the summer, this is an especially important task.

Luckily, Multnomah Falls sits just off the Historic Columbia River Highway, and stunning photos can be taken a few steps from the car. Head towards Benson Bridge for a closer view of the falls and feel the cooling mist against your face.

Once you’ve taken all your pictures, venture down the Multnomah-Wahkeena Loop for one last day of waterfall chasing before flying out of Portland. The trail meanders about 5 miles through old-growth forests, crosses trickling streams, and passes basalt walls. Some of the waterfalls you’ll find on the loop include Wahkeena Falls, Dutchman Falls, Wiesendanger Falls, Ecola Falls, and Fairy Falls.

After completing the loop, it’s time to make the 30-minute drive back to Portland and get ready to depart.

Places for Next Time

If you followed this 10-day itinerary, I’m sure it was the thrill of a lifetime discovering Oregon’s natural beauty. Believe it or not, this only scratches the surface to the uncountable number of beautiful destinations across the state. If you have time to extend this itinerary or take another Oregon road trip soon, there are lots of other places to consider. Here is also my recommendation for 21 Best Day Trips from Portland.

Eastern Oregon is incredibly far from Portland, and it’s possible to create a road trip through this region alone. From the snow-capped Wallowa Mountains to the barren landscape of Alvord Desert, it’s a nature lover’s paradise. Perhaps you wish to follow the rest of the Oregon Coast since we made a detour back to the Cascades. There are tons of coastal communities that each have something special to offer.

Wherever you decide to go next, any road trip through Oregon is sure to be filled with unforgettable adventures.

What are you most looking forward to seeing on this Portland Road Trip? Let me know in the comments below.

Written by Daniel G