Oregon Road Trip Itinerary
+ Top Attractions

Oregon's capital city of Portland is located just south of the Washington border and over 60 miles (100 km) inland from the Pacific Coast. Portland has a renowned nightlife scene, with the most popular areas being Downtown Portland, Morrison Street, and Burnside Street. In these areas you'll find many great breweries, restaurants, and bars.

Downtown Portland hosts the tranquil Lan Su Chinese Garden, the Portland Art Museum, and Powell's City of Books, a massive multi-leveled bookstore that's quite famous.

One of Portland's top sights in the hills above the city is the chateau-stye Pittock Mansion with its fancy historic interiors and excellent views overlooking Downtown Portland. Nearby are two lush and beautiful gardens, the Portland Japanese Garden and International Rose Test Garden. On the northeastern side of Portland is Rocky Butte Park, which offers excellent views overlooking Portland and both Mt. St. Helens and Mt. Hood on a clear day.

The Columbia River Gorge separates the state of Washington on the northern side, and Oregon on the southern side of the river. On the Oregon side of the river gorge you'll find many stunning massive waterfalls surrounded by lush dense forests, connected via the Historic Columbia River Highway.

Heading east from Portland you'll encounter the Crown Point Vista House, which overlooks a picturesque section of the Columbia River Gorge from high above.

Approximately 1 hour south of Portland is Silver Falls State Park, so be sure to get an early start on the day in order to visit this beautiful place. Silver Falls State Park is a miniature rainforest ecosystem featuring several huge waterfalls amongst an incredibly lush green landscape, with all of the waterfalls connected by a single creek.

To see all of the waterfalls you can hike the popular Trail of Ten Falls, which connects all of the park's waterfalls via an extremely scenic 7.2 mile (11.6 km) hike through this rainforest-like environment. Alternatively you can see some of the park's largest and most notable waterfalls with a much shorter amount of hiking.

The city of Bend is set in the high desert of Central Oregon surrounded by a vast volcanic landscape. The city is a great base from which to explore the incredible natural wonders in the area. The city's historic downtown area is known as Old Bend and hosts many great shops and restaurants. Bend is also home to the last remaining Blockbuster Video as well as the Deschutes Brewery. You can enjoy views over the city from atop the Pilot Butte.

Just west of Bend is the majestic Tumalo Falls. To the north of Bend is Smith Rock State Park, an immensely beautiful volcanic landscape of tall sheer cliffs which are great for rock climbing or hiking. The Crooked River flows around the center of the park, creating a giant peninsula.

South of Bend is the Newberry National Volcanic Monument, which hosts several large cinder cones amongst a black volcanic landscape. Popular attractions in the monument include the Big Obsidian Flow Trail, Paulina Creek Falls, the Lava River Cave, and the High Desert Museum.

The gorgeous Crater Lake National Park is centered around a massive deep blue lake which sits inside of a vast crater, surrounded by beautiful mountains and forest.

You can drive around the vast Crater Lake to enjoy multiple perspectives over this gorgeous natural wonder, most notably Meriam Point, the Watchman Overlook which looks out directly over Wizard Island, and the Sinnott Memorial Observation Station in Rim Village. From Rim Village you can take the short hike up to one of the lake's best viewpoints atop Garfield Peak.

On the northern side of Crater Lake you can hike down to the lakeshore via the Cleetwood Cove Trail, which also leads to the lake's boat tour dock, although these tours must be made far in advance.

Oregon's southern coast features several extremely scenic areas located along Highway 101, although the entire drive along the coast is quite scenic. This route follows along a stretch of this highway between Brookings, OR just north of the California border and Yachats, OR, which is located near the center of the Oregon Coast.

Oregon's northern coast hosts a variety of scenic viewpoints and attractions along Highway 101. This route follows a long stretch of this highway between Newport, OR near the center of the Oregon Coast and Astoria, OR near the northwestern tip of Oregon.