Exploring Portland and beyond: 8 top destinations in Oregon

While many envision Oregon as a vast forest or associate the Pacific Northwest solely with Portland—its delightfully quirky and largest city—this expansive state has so much more to offer.

Whether you seek outdoor thrills or are more inclined toward culinary delights and fine wines, Oregon has a wealth of experiences awaiting you. Here’s our guide to the top destinations and reasons to explore them.

1. Portland

The ultimate destination for food enthusiasts

Portland serves as many people's gateway to Oregon, boasting the title of the state’s largest—and most eccentric—city, filled with attractions. Here, you'll discover the finest museums and public parks, along with the renowned Powell’s City of Books nestled in the city center. As a nationally acclaimed culinary destination, many flock to the City of Roses with a primary goal: indulging in its food scene. Known for its vibrant street food culture featuring hundreds of food carts, Portland also has a sophisticated dining side, with upscale restaurants like the James Beard Award-winning Haitian eatery kann attracting visitors from across the USA and beyond. This article can barely scratch the surface of Portland’s culinary gems, so check out our recommendations for the top locally-owned and beloved eateries in Portland.

Insider tip: If you’re planning a culinary adventure in Portland, keep in mind that many local restaurants take Mondays and Tuesdays off.

2. The Oregon Coast

Top destination for breathtaking scenic drives

The Oregon Coast is a stunningly beautiful region that defies the typical beach getaway. Forget the stereotype of sunbathing on crowded sands; here, you can explore nearly 400 miles of public coastline adorned with towering cliffs, wind-swept conifers, and expansive sandy beaches that often feel like your own private paradise. This area is a haven for nature lovers, with numerous parks and natural spots—including the Cape Perpetua Scenic Area and Humbug Mountain State Park—inviting hikers and campers to immerse themselves in the stunning surroundings.

Travel advice: While it's possible to drive the entire Oregon Coast in a single day, it's highly recommended to take your time. This region deserves leisurely drives with plenty of opportunities to stop and soak in the spectacular views.

Excited to plan your adventure in Oregon? Discover the top activities to enjoy during your visit

3. The Columbia River Gorge

Ideal destination for hikers

While it’s hard to crown any single area as Oregon's most picturesque, the Columbia River Gorge certainly ranks among the top. Stretching across both Oregon and Washington, the Gorge hugs the Columbia River, which partially separates the two states. It’s a wonderful spot for day hikes, with most trailheads just a 30 to 45-minute drive from downtown Portland. Even if you prefer a more relaxed visit, don’t miss the chance to see Multnomah Falls, the tallest waterfall in the state, or enjoy the stunning views from the Vista House, a beautifully designed rest area in the art nouveau style.

Travel advice: The Gorge can become extremely crowded on summer weekends, so it's best to avoid these times if you can. If you must go, try to arrive early to secure a parking spot.

4. Eugene

Best destination for runners and cyclists

Known as 'Track Town USA,' Eugene is celebrated as a hub for track and field, hosting a variety of running events, especially during the summer months. It's also an ideal spot for casual joggers, offering a wealth of trails with a delightful mix of flat and hilly terrain. Cyclists will appreciate the city's extensive bike lanes, including the Ruth Bascom Riverbank Trail System, which weaves through the expansive Alton Baker Park, making it easy to navigate on two wheels.

5. The Willamette Valley

Best destination for wine enthusiasts

You don't have to travel to France, Italy, or even California's Napa Valley to indulge in the world of wine. Oregon's Willamette Valley stands out as one of the finest places for wine tasting in the nation. Stretching from just south of Portland down to Eugene, this picturesque region boasts rolling hills adorned with vineyards, charming bistros, and inviting bed and breakfasts. Best of all, tasting fees are generally lower compared to other regions, often waived with the purchase of a few bottles. If you're considering a trip to Willamette Valley, don't miss our first timer's guide to the area.

Planning tip: The late summer is ideal for visiting, with lovely weather and vibrant grapes on the vines. If your visit coincides with harvest season (typically September and October), be prepared for potential delays due to slow-moving farm machinery on rural roads.

6. Bend

Best destination for year-round adventurers

The Central Oregon city of Bend is a haven for outdoor enthusiasts, benefiting from a drier and sunnier climate compared to the western part of the state. In winter, it attracts skiers and snowboarders thanks to its close proximity to Mt. Bachelor, but it's an even better base for summer adventures. Popular activities include rafting on the Deschutes River and embarking on backpacking trips in the Three Sisters Wilderness. Additionally, Bend is a short drive from Smith Rock, renowned as one of the premier rock climbing spots in Oregon.

Plan your Oregon trip perfectly with our seasonal guide

7. Crater Lake National Park

Best destination for lake enthusiasts

Home to the deepest lake in the United States, Crater Lake National Park is Oregon's sole national park. A must-do is a boat trip to Wizard Island, a cinder cone island at the heart of the caldera. Additionally, a scenic drive along Rim Drive, a 33-mile loop, provides stunning views of Crater Lake from all perspectives. For breathtaking vistas of both the lake and the surrounding forests, hike the 3.4-mile trail up Garfield Peak, which starts at the park's Rim Village.

Planning tip: Due to its popularity, Crater Lake National Park's campsites and accommodations often book up well in advance, so be sure to reserve early. If you can't find a spot, consider staying at nearby Diamond Lake, conveniently located a short drive from the national park.

8. Ashland

Best destination for theater enthusiasts

Located just a short drive from the California border, the city of Ashland in Southern Oregon is renowned for the Oregon Shakespeare Festival, a theater company that has been showcasing the Bard's works since 1935. The festival runs for most of the year, pausing during the colder winter months, and features a robust lineup of Shakespeare's classics along with various works from other playwrights. For more ideas on what to do in Ashland, explore our guide to this vibrant city.