The Ultimate Oregon Road Trip

The Ultimate Oregon Road Trip

12 days, tons of sights—get ready for the drive of a lifetime

written by Sheila G. Miller

AFTER BEING COOPED UP, hitting the open road can be invigorating.

The past few months have been a trying time for all of us. But there’s no balm like the outdoors to soothe anxiety and give us a renewed sense of self.

We spent some time trying to construct the ultimate Oregon road trip—that is, a twelve-day trip that takes you through the natural wonders of our state. From the dunes of the Oregon Coast to the jagged edges of the Wallowas, we tried to hit them all. For now, reopening our state to tourism is uncertain, so some of this may continue to be a pipe dream. But that doesn’t mean we can’t plan and dream—join us, won’t you?

Get up close and personal with Central Oregon’s volcanic past at Newberry National Monument.

Steve Heinrichs

DAY 1

Bend is in the center of the state, making for a perfect place to start and end the journey. It’s a city that has become something of a celebrity over the past decade or two, and so you’ll want to explore—a walk along the Deschutes River (if you swing past the Bend Whitewater Park you’ll likely spy surfers on the manmade wave) and a beer at one of the city’s dozens of breweries are a perfect locals’ way to enjoy the day. If it’s warm enough, you can float the river through town and end at Drake Park, then walk into downtown for some of the city’s excellent food—Barrio for a taco fix, Bos Taurus for a fancy steak, Zydeco Kitchen + Cocktails for everything, but especially the shrimp and grits starter.

Mt. Bachelor is a short trip away, as are tons of mountain biking trails. If you didn’t throw a bike on the back of your car, no stress— bike shops like Pine Mountain Sports will get you kitted out. Finish your day with a sunset beer at Crux Fermentation Project, which offers happy hour in line with the time when the sun goes down. Then rest your head at the Oxford Hotel downtown, or camp nearby at Tumalo State Park.

Bend is the starting point of our epic journey.

COVA

Bend Whitewater Park has a manmade wave for surfing the river.

Bend Park & Recreation District

DAY 2

You’ll travel only a short distance today, but it’s for a doozy of a sight—Smith Rock State Park. Drive through Redmond in the morning and grab a liege waffle and a latte at Proust Coffee, then head north to Terrebonne, about forty minutes from Bend. Smith Rock is a mecca for rock climbers. If that’s you, bring your gear. If it’s not, know there are lots of hiking trails here, and if you’re prepared you’ll be able to hoof it up Misery Ridge for some epic views.

Either way, you’ll want to spend some time checking out the incredible scenery—spires and rock faces jutting from the ground in a most dramatic fashion. When you’ve had enough, you can lunch at nearby Terrebonne Depot or head on to Prineville.

Smith Rock State Park is a rock-climbing mecca.

COVA

Prineville is a western outpost with the coolest courthouse.

COVA

Prineville offers a feeling of small-town Oregon that is easy to forget still exists, especially east of the Cascades. This city has arguably the prettiest county courthouse in Oregon, and across the street one of the great diners of all time—the Tastee Treet. Grab an ice cream cone, then explore the downtown. When it’s time to bed down, you can camp on public lands in the area, check in at the hip New Hotel Redmond or swing out to Brasada Ranch for a night of pampering. Warning: Brasada is so amazing that if you stay there, you may not want to continue this trip.

Steins Pillar, near Prineville, is part of Central Oregon’s outdoor beauty.

Amanda Luelling

DAY 3

You’re headed east today, to a place in Oregon that few visit—the Pillars of Rome, the Owyhee River and the Alvord Desert. It’s a long trip, but trust us when we say it’s worth it. Head southeast on Highway 20 to Burns, then down Highway 78. Make sure you check the weather before heading out onto the Alvord Desert—its cracked dry ground can turn to mud quickly when it rains, and you do not want to get stuck, because this is only Day 3! This dry lake bed runs about 12 miles and receives very little rain each year. It’s just east of Steens Mountain, which overlooks the dry landscape. This is prime Instagram territory, friends. Soak in the Alvord Hot Springs ($5) nearby, then head out onto the playa.

The Alvord Desert is an atypical Oregon landscape.

Jim Meyers/Vertizon Photography

Then you’ll want to get back on the road to see the Pillars of Rome, which is about one and a half hours north and east of the desert. Here, you’ll find 100-foot-high rock formations that reminded settlers of the ancient Italian city. It’s an incredible sight, and if you are a photographer, you’ll want to watch how the light hits the pillars.

You can camp in this area, or you can keep going and check out the Owyhee Wild and Scenic River, which meanders through southeastern Oregon and into Idaho. Along the way, there are high canyon walls, hot springs and spires. There are plenty of secluded camping sites—pick your poison.

Paddlers on the Owyhee.

Jim Meyers/Vertizon Photography

DAY 4

After this camping experience, you’ll be ready for some indulgence. You’ll have a long drive, but it’ll be worth it when you arrive in the northeastern edge of Oregon, in Joseph. En route, if you haven’t seen enough of the Owyhee River’s incredible beauty, set off for Leslie Gulch, Succor Creek State Natural Area and Lake Owyhee State Park. They’re not really on the way, but the region is remarkably beautiful, and you’re unlikely to make it out this way again anytime soon, right?

Leslie Gulch is a must-see on the Owyhee.

Jim Meyers/Vertizon Photography

Time to see another unreal Oregon sight before you head into the luxury of a small-town boutique hotel: Hells Canyon. You’ll hook up to I-95 north and it will take you to the canyon, which is the deepest river canyon in North America. It’s 8,000 feet down to the Snake River in its deepest places, and it’s basically Oregon’s Grand Canyon. From there, it’s less than two hours to Joseph. Get your pamper on at The Jennings Hotel. You’ve earned it.

DAY 5

Wake up to Joseph’s adorable downtown and its incredible Wallowa Mountains views. If you have a hankering for a hike, the wilderness here is very close to town and is easy to get into. Then you’ll want to head to Wallowa Lake State Park and to Vali’s Alpine Restaurant for a meal you won’t soon forget—we’re talking chicken and dumplings, paprikash, and if you plan ahead, doughnuts. Check with the restaurant on times before driving out there.

The Wallowas soar over the landscape.

Marley Henderson

When it’s time to hit the road, you’ll go west—it’s four and a half hours to Hood River, and on the way you’ll be treated first to endless farm fields, before those give way to the Columbia River Gorge and its windy, wonderful scenes.

When you arrive in Hood River, you’ll be treated to vistas of the choppy Columbia River, colorfully dressed windsurfers riding the river. Depending on how long you plan to stick around, you can make a few stops on the Fruit Loop, grabbing some fresh fruit, jams and wine for your journey. Back in town, stroll along the river and grab some pizza for dinner at Solstice Wood Fire Cafe & Bar, and a beer at Double Mountain Brewery. Enjoy the beds and the history at the Historic Hood River Hotel.

Hood River’s Fruit Loop is the spot for snacks.

Austin Smith

DAY 6

Once you’ve had your fill of Hood River (is it even possible?) and especially Broder Øst’s Nordic brunch, you’ve got a scenic drive ahead of you—you’re going to Portland. It’s not a long drive, but there are multiple places you’re going to want to stop to ooh and ahh, as well as detours that will give you the full Oregon experience.

Timberline Lodge is about an hour south of Hood River, so if you’ve never seen this Platonic ideal of a lodge before, it’s definitely a detour worth making— plus you’ll get to enjoy the wonder of Mount Hood and its surrounds.

If seeing the mountain from afar is enough for you, then head out on the Historic Columbia River Highway Scenic Byway. The road, which has reopened since the 2017 Eagle Creek Fire laid waste to the area, offers bendy curves, tons of waterfalls and epic views. The Vista House at the Crown Point State Scenic Corridor may be closed, but there are lots of other spots to grab a good view of the Gorge.

Vista House at Crown Point, if open, is a great spot to see the Gorge.

Friends of Vista House

When you’ve hiked to every waterfall you can find, hit the road for Portland, which is an hour or so away from Hood River. In Portland, there are hotels, restaurants and entertainment options galore. Revel in this big-city life for a day or two, because soon you’ll hit the road again.

DAY 7

Portland beckons for a day or more. For a perfect day there, we’d stay at Hotel Zags, which is centrally located in downtown Portland and has a gear shed of all kinds of useful items to improve your vacation. From there, it’s an easy trip up to Powell’s City of Books for some roadtrip reads, to Forest Park for a quiet and muddy hike, or across the river to the east side—where foodie dreams come true. Note: Because this is Portland, there are also dozens of incredible restaurants on the west side of the river as well.

Portland’s Powell’s Books is always a required stop.

Travel Portland

Forest Park is the city’s urban green space.

Bruce MacGregor

Get your meat fix at Ox or Olympia Provisions, some barbecue at Matt’s BBQ, upscale French at Le Pigeon, Russian at Kachka … we’re just skimming the surface. Create your own mini pub crawl with stops at Great Notion, Gigantic, Baerlic, Ecliptic, Little Beast … really, the world is your oyster here. If you’re road-tripped out, you could stay in Portland for the next few days and visit the Portland Art Museum and the Oregon Museum of Science and Industry if they have reopened, or wander some of the many outdoor options nearby.

DAY 8

When big-city life begins to wear on you—onward, to the coast! Take the Sunset Highway all the way to the Pacific Ocean and find Cannon Beach, which offers iconic views and is only an hour and a half from Portland. Make it your home base as you explore the northern coast.

Here you’ll find what is maybe Oregon’s mostphotographed natural wonder—Haystack Rock. But that’s really just the beginning of the wonders of the northern Oregon Coast. Swing up to Astoria for views and brews at Fort George Brewery, enjoy the kitsch (I’m talking bumper cars) of Seaside, or hike through the forests and along the sand—Ecola State Park is currently under an emergency closure, but lots of other areas remain open, including Oswald West State Park. Stretch your legs on miles of quiet coastline, then head back into Cannon Beach for a quality meal at The Bistro. Then gear up for another day of beautiful driving.

Enjoy the kitsch of Seaside.

Don Frank

DAY 9

It’s time to head south, the Pacific Ocean to your right the entire way. The Pacific Coast Scenic Byway winds along the coast for the entire length of Oregon. Along the way, you’ll want to stop at Tillamook Creamery for a self-guided tour of cheesemaking (and free samples), peer into the tidepools at Cape Kiwanda in Pacific City, and zoom past Lincoln City while checking out the kites flown on windy days. Grab a bowl of chowder at Gracie’s Sea Hag in Depoe Bay. Keep heading south and find the Oregon Coast Aquarium in Newport and the Sea Lion Caves outside Florence. If you’ve never seen (and smelled) Steller sea lions in the wild, this is a must.

Cape Kiwanda in Pacific City has tidepools and views.

Marley Henderson

Steller sea lions at the Sea Lion Caves never disappoint.

Then it’s on to the Oregon Dunes National Scenic Area, near Coos Bay, which offers stunning views of hilly sand dunes as far as the eye can see. It’s mesmerizing—get out on the dunes in a dune buggy or four-wheeler for an incredible experience.

Then point your car toward Bandon and spend the night in luxury at Bandon Dunes Golf Resort. The views of the ocean are incredible, and if you’re a golfer, this is not a minute to be squandered. Get on these fairways.

The Oregon Dunes National Scenic Area is mesmerizing.

Oregon’s Adventure Coast

DAY 10

Our next stop is proof that culture can be very much alive in small towns. In a normal year, Ashland would be the spot for a Shakespeare infusion. This is no normal year, but Ashland is worth visiting even without the Oregon Shakespeare Festival’s draw. You’ll take Highway 42 east, then I-5 south to reach this charmer of a city about three hours away. If you’d like to spice up your drive a bit, check out the area’s excellent wineries. Tasting rooms abound along this route, from Kriselle Cellars in White City to DANCIN Vineyards outside Medford to Cliff Creek Cellars in Gold Hill.

Ashland is worth visiting even if the Oregon Shakespeare Festival is cancelled this year.

T. Charles Erickson

When you get to Ashland, settle in at one of our favorite hotels—either Ashland Springs Hotel in the heart of the city and walking distance to the Oregon Shakespeare Festival’s Angus Bowmer Theatre, or Ashland Hills Hotel, which sits glamorously at the edge of town.

Wander Lithia Park and plan to return when you can sit in the round for “A Midsummer Night’s Dream.”

DAY 11

Crater Lake is Oregon’s only national park.

Xanterra Travel Collection

We may have saved the best for last. Just an hour and a half from Ashland is Oregon’s only national park. And what a special place it is. Crater Lake National Park is the United States’ deepest, and arguably bluest. Fed by snow and rainfall, the lake sits like a jewel in the middle of high cliffs, Wizard Island winking from the western side of the water. There’s plenty of terrain here to get out and get some fresh air. When the park has reopened, drive around the lake, depending on snow levels (the north entrance and West Rim Drive typically open in May or June, while the East Rim Drive can sometimes be covered in snow until late July). If snow levels remain high, snowshoe through the area. Two-hour boat cruises through the lake typically begin in July.

There’s also just something soothing about grabbing a drink or lunch at Crater Lake Lodge and spending some time in the rocking chairs outside the lodge. Stay overnight at the lodge, or in a campground nearby.

DAY 12

All good things must come to an end. What better way to soften the blow than with the short drive from Crater Lake to Bend, with stops at Newberry National Monument and some beers to watch the sunset?

The drive takes about two hours, but there’s plenty to do on the way into town. The Newberry National Monument has endless options— walk through lava fields, visit Paulina Falls, or hike through the Lava River Cave or Lava Cast Forest. All are easily accessed and perfect ways to get outdoors before returning to the real world.

A stop at Newberry National Monument eases you into the end of your road trip.

Steve Heinrichs

When it’s time to head back into Bend, do so gently, with dinner and a beer on the lawn at Bend Brewing Co., the Deschutes River moving slowly past you. Remember: adventure in Oregon is never really over.