Planning a road trip through Oregon? We don’t blame you: The Beaver State is home to dramatic landscapes that include rugged rock formations on the Oregon Coast, lush forests and thundering waterfalls in the Columbia River Gorge, expansive high deserts in Central Oregon, and the impossibly blue hue of Crater Lake.
If you’re looking for help planning a memorable road trip through Oregon, we’ve put together a suggested itinerary—complete with friendly towns and cities, iconic attractions, and must-see sites—to help make the most of your epic Oregon road trip:
Day 1: Starting a Road Trip in Portland
Your Oregon road trip itinerary begins by flying into Portland International Airport (airport code PDX), picking up a vehicle from one of several on-site car rental companies, and heading east toward the Columbia River Gorge or Mount Hood.
If you head east, traveling into the heart of the Gorge via Interstate 84, make time for the curvy Historic Columbia River Highway, which was built in the early 1900s and remains a fun drive today; sweeping viewpoints of the broader gorge and numerous waterfalls await along the way. You’ll pass the 620-foot-tall Multnomah Falls, which is among the tallest waterfalls in Oregon and one of the state’s most-visited natural sites. After 60 to 90 minutes (sans stops), you’ll arrive in the community of Hood River—where creative craft breweries, outdoor recreation, and a charming downtown core await. When it’s time to head toward Central Oregon, you’ll drive south through the Hood River Valley via Highway 35—passing several farms along the Hood River Fruit Loop en route.
Otherwise, you can take Highway 26 out of Portland, onto the slopes of Mount Hood, and toward the community of Government Camp. Hundreds of miles of hiking and biking trails, forested lakes, and other outdoor opportunities sprawl out across the Mt. Hood National Forest; one of the region’s top sites is Trillium Lake, which boasts wide-open views of Oregon’s tallest peak. (In summer, Mt. Hood Outfitters provides kayak and stand-up paddleboard rentals at Trillium Lake.) Spend the night at Timberline Lodge, a regal ski lodge that opened in 1938 and is today an iconic site on Mount Hood.
Day 2-6: Discover Central Oregon
Getting to Central Oregon from Hood River or Mount Hood is easy. From Hood River, it’s about a three-hour drive to Bend (the largest city in Central Oregon); from Government Camp, it’s about a two-hour drive to Bend.
As you descend from the forested slopes of Mount Hood, you’ll arrive in the high desert. Ancient juniper trees, khaki-colored rock formations, and sagebrush bushes dot the horizons on either side of the highway, and Cascade peaks (including Mount Jefferson) tower over it all to the west.
You can’t go wrong booking a stay in any of the communities we’ve outlined below—get inspired with a look at places to stay in Central Oregon—and we’d suggest picking and choosing which activities look the most fun to piece together a fun four- or five-day trip in the region.
Enjoy a Mix of Urban Chic and Natural Wonder Around Bend
When you visit Bend, you’ll find yourself immersed in some of Central Oregon’s top sites, restaurants, brewpubs, and attractions. Just south of downtown, Drake Park hosts walking trails and plenty of space to stretch out along the Deschutes River. If you’re visiting in summer and are up for a drive, check out our guide to the Cascade Lakes Scenic Byway for tips on driving the dramatic highway into the heart of the Cascade Range—where you’ll be surrounded by snow-capped mountain peaks, crystal-clear lakes, quiet campgrounds, and dozens of hiking trails. (If the views are what brought you to our state, learn more about Oregon scenic byways.) After a busy day, find a great meal at one of the top restaurants in Bend—and get to know the world-class breweries and cideries across the city.
Explore the Cascades Around Sisters
Roughly 24 miles northwest of Bend, the Old West-inspired community of Sisters sits at the foot of the Cascade Range and provides plenty of fun in and around town. In winter, hit the slopes at Hoodoo Ski Area; there, you’ll find more than 800 acres of terrain and the region’s only night skiing. In summer, the McKenzie Pass Highway heads southwest from Sisters and into the Cascade Range, where you’ll drive past lakes, lava flows, old-growth forests, and more—all in the shadow of more than a dozen mountain peaks. Around town, take time to peruse some of the many art galleries that contribute to a thriving creative scene in Sisters.
For more ideas on what to do in Sisters and beyond, check out our guide to the top attractions in Central Oregon.
Escape Into Oregon’s High Desert Around Redmond
Roughly 18 miles north of Bend, the fast-growing city of Redmond offers plenty of fun for visitors from all walks of life. For families, check out Sam Johnson Park near downtown; the park hosts the wheelchair-accessible Hope Playground and other engaging activities for little ones. Further west, Cline Falls State Scenic Viewpoint is home to a short hiking trail that leads to an overlook of a 20-foot cascade in the Deschutes River. When the day is done, stroll through downtown Redmond, where you’ll pass historic brick buildings that host restaurants, shops, and other fun stores.
Just outside of town sits Smith Rock State Park—whose sheer rock faces gave birth to sport climbing in the United States in the 1980s; today, the park’s hiking trails, sweeping views, and climbing routes are some of the top things to do in Central Oregon.
See the Dazzling Painted Hills
Further east is the Painted Hills Unit of the John Day Fossil Beds National Monument, which is about two hours northeast of Bend.
The wider monument is broken up into three disparate units, but the Painted Hills Unit is the most famous and busiest of the three. That’s where you’ll find colorful hillsides of red, black, yellow, and brown—the product of millions of years of volcanic activity, changing climates, and steady erosion. Five trails, totaling just shy of three miles in all, invite visitors to enjoy the best viewpoints. Be sure to stay on the boardwalk or trail at all times, since footprints can remain for months or years in the colorful dirt.
Day 7: Stay the Night at Crater Lake
Crater Lake National Park sits high in the Southern Oregon Cascade Range, and the heart of Oregon’s only national park is its namesake reservoir. Crater Lake is the deepest lake in the United States, reaching more than 1,940 feet at its deepest point, and sits within the hollowed-out caldera of a volcano that erupted more than 7,700 years ago. The park’s northern entrance station—typically open June to October, depending on seasonal snowfall—sits about 90 miles southwest of Bend.
In summer, the 33-mile Rim Drive circles Crater Lake. Dozens of roadside pullouts provide views of the lake’s dramatic blue waters from high on the caldera rim, and several hiking trails offer even more impressive sights. Away from the lake, a few visitor centers detail the geological and cultural history of Crater Lake, and the two-mile (round-trip) Plaikni Falls Trail takes hikers to the base of a waterfall that’s surrounded by summertime wildflower blooms. Plan your visit for July or August, when the park is fully open and all trails are typically snow-free.
You have a few options for overnight stays in Crater Lake National Park. The regal Crater Lake Lodge is perched on the lake’s southern shore; reservations usually fill six to 12 months in advance. Seven miles south, The Cabins at Mazama Village are basic but provide a comfortable overnight stay—and Mazama Campground offers a mix of tent and RV sites in a forest of fir, pine, and hemlock. Just outside of the park, choose among cabins and lodge rooms at the historic Union Creek Resort; book a lodge room, cabin, or studio apartment at Diamond Lake Resort; and pitch a tent or park your RV in one of more than 200 sites—including 51 lakeside sites—at Diamond Lake Campground.
Day 8-10: Drive the Oregon Coast back to Portland
Start the final stretch of your road trip with a 3.5-hour drive west to Florence on the Oregon Coast—where you’ll find rugged sea stacks, wide-open bluffs, rocky crags, and old-growth forests of Sitka spruce. Florence sits at the northern edge of the 40-mile-long Oregon Dunes National Recreation Area and hosts a walkable downtown core full of restaurants and pubs, coffee shops, and souvenir stores on the banks of the Siuslaw River.
From Florence, spend the next few days heading north on the scenic Highway 101. A few choice stops include the Oregon Coast Aquarium in Newport (where you’ll see all sorts of native marine life), the Tillamook Creamery (which produces award-winning cheeses and ice cream), the iconic Haystack Rock in Cannon Beach, and the historic, working-class community of Astoria near the mouth of the Columbia River. From Astoria, it’s about 95 miles back to Portland—and the end of your road trip through Oregon.
Tips for Planning Your Oregon Road Trip
Start planning your magical Oregon road trip itinerary with these easy tips:
Best times of year to visit: You can plan an Oregon travel itinerary in all four seasons, but you’ll find the most services available, most often, from late spring to early fall. Between Memorial Day and mid-September, businesses (such as restaurants and souvenir shops) are typically open more often, trails tend to be snow-free, and the risk of snow and other adverse weather events is substantially lower.
What to pack: In all seasons, it helps to dress in layers to plan for changing weather. Bring a water-resistant shell to account for rainfall (a possibility all year long), a comfortable outer layer for trips to food cart pods and craft breweries, and a moisture-wicking base layer that’ll keep you cool on hiking and mountain biking trails. A puffy jacket can’t hurt, either, especially when the sun goes down in the high desert. And in Central Oregon, which enjoys roughly 300 days of sunshine per year, you’ll be glad to pack along plenty of sunblock.
Road conditions: No matter when you visit, it’s always a good idea to check road conditions ahead of time. TripCheck – Oregon Traveler Information is an official resource from the Oregon Department of Transportation; the interactive map showcases webcams, provides traffic alerts, details delays and closures, and provides other helpful information to make the most of your Oregon road trip.
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