Top Road Trips in Oregon with iBestTravel

What’s the best way to experience Oregon’s gorgeous scenery? From the open road.

The state’s myriad landscapes are like a playlist of Mother Nature’s greatest hits. In a single day, you can drive from the high desert to the Pacific Ocean, passing through forests, vineyards, and mountains along the way. Stops on the route might involve sipping wine, exploring caves, and taking in a national park.

Whether you’re searching for a scenic driving route or a multi-day road-trip extravaganza, these top road trips in Oregon will fuel your next adventure.

1. Oregon Wine Country

Best road trip for wine and culinary experiences
Portland to Salem; 47 miles (76 km)

Oregon is home to over 900 wineries, most nestled in the hills of the Willamette Valley. Take to the road to visit a few. Kick off in Portland, where you can sip on local varietals from various winemaking members. Just over an hour away, McMinnville has more than 20 downtown tasting rooms, with plentiful options in close proximity. Highlights in this area include the renowned Burgundy-style bottles at Resonance Wines’ tasting rooms in Carlton and Dundee Hills. Afterward, head to Soter Vineyards in Carlton for some of the region’s best bubbles. Conclude the evening with a tasting menu centered around wild local mushrooms at a local restaurant.

End this road trip itinerary at the state capital of Salem. For a unique spin on the tasting-room experience, sample different varieties of local single-flower honey at a small local ranch. Wineries in this area include a lovely family-owned estate.

Planning tip: The Oregon Truffle Festival showcases the Willamette Valley’s prized wild delicacy between February and March.

2. Crater Lake

Best road trip for experiencing Oregon’s only national park
Bend to Klamath Falls; 154 miles (248 km)

Bend, the start of this road-trip itinerary, is the outdoor-recreation capital of Oregon. The high-desert areas in the center of the state showcase geological wonders, including underground lava tubes just outside town. Spelunking, rafting, fly fishing, kayaking, hiking, and climbing are popular activities here.

Some 90 minutes from Bend, Crater Lake National Park – Oregon’s lone entry on the national park roster – is home to the deepest lake in the USA. A bright blue sapphire in the wilderness, Crater Lake plunges to depths of 1943 ft (592 m). The Scenic Rim Drive encircles the lake, offering extraordinary vistas. This 33-mile loop showcases waterfalls, hiking trails, and picnic spots. In summer, boat rides are available.

After exploring Crater Lake, finish the itinerary at a resort in Klamath Falls, where you can enjoy a golf course and spa services.

Planning tip: Crater Lake National Park receives more than 40 inches of snow in winter, affecting travel, so check the park’s website for updates.

3. Mt Hood Scenic Byway

Best road trip for mountains and fruit trees
Hood River to Troutdale; 105 miles (169 km)

This itinerary begins in Hood River, where Mt Hood rises majestically. Windsurfing and kiteboarding are popular here, and the scenery is breathtaking. Hood River offers shops, breweries, and a range of dining options, with historic accommodations available for various budgets.

Travel south to the Hood River Valley to see stunning views, especially during spring when fruit trees blossom. Next, stop by Timberline Lodge in Government Camp to admire its unique architecture.

Before concluding this trip in Troutdale, mountain bikers should explore the Sandy Ridge Trail System, featuring trails suitable for all skill levels.

Planning tip: If you’re visiting after summer, consider bringing your skis; the snow season typically runs from November through May.

4. Columbia River Scenic Byway

Best road trip for waterfalls and scenery
Troutdale to The Dalles; 70 miles (113 km)

The Historic Columbia River Highway was constructed over 100 years ago to provide access to the breathtaking scenery of the Columbia River Gorge, now Oregon’s largest national scenic area. Head from Troutdale to the 100-year-old Crown Point Vista House for magnificent views of the river.

The route is also famous for its waterfalls, with Multnomah Falls being the highest at 620 ft (189 m). After a quick lunch in Hood River, explore the quaint downtown area filled with unique shops and galleries.

The trip concludes at the Columbia Gorge Discovery Center and Museum in The Dalles, where exhibits highlight the area’s rich geological and historical heritage.

Planning tip: In The Dalles, don’t miss the colorful murals depicting the region’s rich history.

5. The Oregon Coast

Best road trip for beaches and ocean views
Astoria to Brookings; 363 miles (584 km)

The 363-mile Oregon Coast Scenic Byway follows the Pacific Ocean’s shoreline. Start in Astoria, with stunning views at the Astoria Column. Seaside is an excellent location for classic beach-town activities, and Cannon Beach offers breathtaking views of Haystack Rock.

Along the coast, attractions include free tours at local creameries, historic lighthouses, and magnificent natural sites like the Oregon Dunes National Recreation Area.

When you reach Brookings, spend an afternoon meandering through a grove of towering redwoods on a scenic trail.

Planning tip: Lodging can be expensive in summer, so consider visiting before Memorial Day or after Labor Day for better rates.

Keep Planning Your Trip to Oregon

Oregon’s diverse landscapes and attractions await your exploration. Happy travels with iBestTravel!

This article was first published on September 16, 2021, and updated on April 28, 2024.