As the gateway to the Pacific Northwest, Oregon offers visitors a broad range of activities, from coastal viewpoints to volcanic peaks to rolling hills flush with vineyards.

If you’re willing to drive (and drive a lot), there are a slew of trips that each provide their own uniquely Oregon experience, whether you’re looking for outdoor scenery, extreme adventure, or a dose of literary and culinary history. From scenic day trips to multi-day excursions, here are our favorite road trips in Oregon.

Wallowa Mountain Loop Road
Take time out from your Oregon road trip to appreciate the beauty of Wallowa Mountain © Different_Brian / Getty Images / iStockphoto

Hells Canyon Scenic Byway

Best road trip for scenic photographers
Start – La Grande; End – Baker City; Distance – 213 miles

For the family looking for a long weekend escape or the adventurous #vanlife couple angling for that next great travel vlog, the Wallowa Mountains and Hells Canyon Scenic Byway are bristling with opportunities for road-trippers who enjoy an active respite from the hours on the asphalt.

Winding mountain roads take you through a handful of Oregon’s most iconic small towns, including La Grande, Joseph (bonus points if you listen to the band of the same name on your way through), and concluding in Baker City.

Midway through the trip, be sure to stop off at Wallowa Lake State Park, home of the impressive Wallowa Mountain Range, and a large part of what makes this one of the best road trips in Oregon. Nicknamed “Little Switzerland” for its pristine glacial peaks and fresh alpine air, Wallowa Lake and the surrounding Eagle Cap Wilderness also feature a tramway, where visitors can ascend to the top of the impressive Mount Howard, over 8000ft above sea level.

Top things to do in Oregon

Hikers at Umpqua Sand Dunes in the Oregon Dunes National Recreation Area on the central Oregon coast
Hikers in the Oregon Dunes National Recreation Area on the central Oregon coast © Greg Vaughn / Alamy Stock Photo

The 101: PNW edition

Best road trip for beachgoers
Start – Bandon; End – Pacific City; Distance – 168.5 miles

Monumental, jagged cliffs overhang crashing waves as seals, whales and other wildlife make their home in the murky blue depths below. The Oregon coast remains one of the most picturesque locations in the country, and, consequently, one of the best road trips for scenery the Beaver state has to offer.

The trip starts in Bandon, a small but oft-mentioned town about 100 miles north of the California border. Play a round at the legendary Bandon Dunes Golf Course (where the PGA Junior Tour is held each year), and try to leave with the same number of golf balls you arrived with.

Next, as the 101 winds its way east from the coastal cliffs, stop off in Florence, an inlet town at the mouth of the Siuslaw River (and only 60 minutes from Eugene), for a night or a weekend spent four-wheeling across the Oregon Dunes National Recreation Area.

For the extra bold, the Siuslaw Dunes Daybreak Racing offers a 25k or 50k footrace that treks across the dunes, the beach, and a forest trail all in the same course. After that, visit Nye’s Beach in Newport, located almost exactly halfway up the Oregon coast, and only an hour outside of Corvallis, home to Oregon State University.

Don’t let your visit pass by without a tour of the Yaquina Head Lighthouse (originally erected in 1871), and keep an eye out for migrating humpback whales in the early fall. The last stop on this epic coastal tour is Pacific City, site of yet another coastal dune and the flagship location of Oregon’s own Pelican Brewing, where guests can sip on hop-laden Pacific Northwest IPAs or the flagship Kiwanda Cream Ale while watching the Dory Boats (a traditional, flat-bottomed boat meant to sit on top of the surf) launch from the shore.

11 best beaches in Oregon

Rows of bookshelves in Powell's bookstore in Portland, Oregon
Start your road trip among the inspirational titles in Powell's Bookstore © George Rose / Getty Images

Trace Oregon’s literary history

The best road trip for book lovers
Start – Bridge of the Gods (Columbia River Gorge); End – Salem; Distance – 87 miles

Whether you’re an Oregon native or just a really big fan of Powell’s Books, this road trip itinerary features the state’s most well-known literary landmarks. The first stop includes a short drive up the Columbia River Gorge to the Bridge of the Gods, where Cheryl Strayed, author of the memoir Wild, finished her inspirational journey on the Pacific Crest Trail. Enjoy fantastic views of the Columbia River, as well as the feeling of being just one degree removed from literary stardom.

Next, venture from the Gorge into Portland, where you can spend time visiting all of the highlighted passages in Beverly Cleary’s Ramona Quimby series, from her iconic home on Klickitat Street to Central Library, where Cleary worked when she first conceived of the novels.

Follow the Multnomah County Library’s “Walking with Ramona” for a full list of locations and the literary events that happened there.

Finish off your real-life book tour by visiting the site of Ken Kesey’s famous novel One Flew Over the Cuckoo's Nest in Salem. While the book was based on an unnamed location in Oregon, the movie was filmed in the Oregon State Hospital, transformed in 2012 into the Oregon State Museum of Mental Health.

Especially eager bibliophiles can also add the State Library of Oregon to their list, located just across town in the historic district.

The 25 best hikes in Oregon

Twin Rocks off the coast at Rockaway Beach
Avoid the crowds at Rockaway Beach © Png-Studio / Getty Images / iStockphoto

Surf & Turf: The Hood to Coast road trip

The best road trip for outdoor enthusiasts
Start – Portland; End – Rockaway Beach; Distance – 222 miles

A long-running PNW sufferfest, the Hood to Coast relay is an annual summer tradition that brings runners across the varied terrain of Oregon’s volcanic peaks all the way to the rocky coast. But, why run when you can drive, and ski, and surf, all in the same day?

While most easily completed from Portland, this road trip itinerary can technically be started anywhere. The first stop is the well-known Mt. Hood Meadows Ski Resort, where skiers, snowboarders and sledders can find skiable snow in season almost six months out of the year. After spending the morning shredding the slopes, trade the bibs for a wetsuit and start your trek to the coast.

Just under three hours away, Rockaway Beach is a somewhat lesser-visited beach with a great local restaurant scene. If you leave the slopes after lunch, you’ll arrive just in time for an evening wave sesh as the sun sets over the scenic coastline. Top off your surf n’ turf day with a surf n’ turf meal at the Old Town Smokehouse, a no-frills seafood joint that’s been impressing locals and tourists alike for decades.

Sun rays through trees on a autumn day at evening sunset in Hood River OR
The views never disappoint in the Pacific Northwest © thyegn / Getty Images / iStockphoto

The Fruit Loop

The best road trip for foodies
Start – Hood River; End – Hood River; Distance – 35 miles

Oregon’s seasonal fruit crops offer a tasty reward to anyone who can make it through the wet winter months. Beginning just above Hood River off of Highway 35, this 35-mile Fruit Loop features 25 different fruit stands, farms and u-pick centers that feature the Pacific Northwest’s finest selection of homegrown fruit.

Start with a fresh pear picking at The Gorge White House, followed by a fresh cider tasting at Fox Tail Cider & Distillery. Move onto lunch at the Packer Orchards & Bakery, and give your lavender picking skills a test at the renowned Hood River Lavender Farm.

Not sure you can do it all in one visit? The beauty of the Fruit Loop is that the fruits vary season to season, making this an easy choice as one of the best road trips in Oregon for foodies and fresh-picking fanatics alike.

Catch fresh Hood Strawberries in the early summer, blackberries and cherries in the middle of July, or the reliably delicious Oregon apples in the fall.

You might also like:

How to hike the Pacific Crest Trail 
7 reasons Bend, Oregon, is the ‘outdoor playground of the west’
Top 10 parks in Portland, Oregon 

Explore related stories

Man Riding Bicycle on Historic Route 66 in New Mexico, USA. Focus on Road Print.; Shutterstock ID 1734099434; your: Brian Healy; gl: 65050; netsuite: Lonely Planet Online Editorial; full: New bike lanes on Route 66
activity, adventure, america, arid climate, backpack, backpacker, bag, bicycle, bike, biker, cycle, cyclist, desert, driving, exercising, explorer, freedom, healthy lifestyle, highway, historic route, horizontal, idyllic, journey, leisure activity, lifestyles, motion, mountains, nature, new mexico, one person, outdoors, people, rider, road, road sign, road trip, route 66, rural scene, southwest usa, sport, tourism, tourist, travel, traveler, united states, usa, wild west, wilderness, young adult


Route 66 is getting a bike-friendly upgrade

May 16, 2023 • 3 min read