Portland and beyond: 8 of the best places to visit in Oregon

Although many people think of Oregon as one big forest — or equate the Pacific Northwest with Portland, its unabashedly weirdest and biggest city — this massive state offers so much more.

Whether you’re a fan of outdoor adventure, or more into food and wine, you’ll find plenty to experience in Oregon. Here's our guide to the best places to go and why you should spend your time there.

1. Portland

Best place for foodies

Portland is most people’s introduction to Oregon, and as the largest (and quirkiest) city in the state, it’s got plenty to see and do. It’s where you’ll find the state’s best museums and public parks, and the celebrated Powell’s City of Books is located right in the heart of the city. Portland is also a nationally recognized culinary hub, and plenty of people travel to the City of Roses with one activity in mind: eating. While it is known for its street food scene, with hundreds of food carts all around town, Portland also has a swankier side, with high-end restaurants such as the James Beard Award-winning Haitian spot kann drawing in visitors from across the USA and beyond. There is hardly room to do justice to all the wonderful places to eat in Portland in this article, so check out our suggestions for all the best locally-owned and loved restaurants in Portland.

Insider tip: If you’re planning a food trip to Portland, be aware that many local restaurants are closed on Mondays and Tuesdays.

2. The Oregon Coast

Best place for scenic drives

Another one of Oregon’s particularly gorgeous areas, the Oregon Coast is not your average beach destination. Throw out all notions of long days lounging on hot sands and instead embrace the opportunity to enjoy nearly 400 miles of public-access coastline fringed with massive cliffs topped with windswept conifers and huge expanses of sand virtually devoid of loungers and tawdry beach cafes. Nature and scenery are the big draws here, with numerous natural areas and state parks – including the Cape Perpetua Scenic Area and Humbug Mountain State Park – enticing hikers and campers.

Planning tip: While you can theoretically drive the Oregon Coast in a day, it’s wise to give yourself a bit more time to explore. This is a region that merits slow drives and lots of extra time to pull over and take in the scenery.

Ready to plan your trip to Oregon? Here are the best things to do while you're there

3. The Columbia River Gorge

Best place for hikers

While it would be unfair to say that one part of Oregon is the most scenic, the Columbia River Gorge is definitely up there. Straddling both the Oregon and Washington sides of the Columbia River (which forms a partial border between the two states), the Gorge as it’s affectionately shortened to, is a fantastic place for day hikes, and most trailheads are within a 30- to 45-minute drive from downtown Portland. Even if you aren’t feeling like exerting much energy, it’s worth visiting to check out Multnomah Falls (the highest waterfall in the state) or to take in the views from the Vista House, a rest area built in the art nouveau style.

Planning tip: Summer weekends in the Gorge get incredibly crowded and are best avoided if possible. If you don’t have any other options, arrive as early as you can to make sure you can at least snag a parking spot.

4. Eugene

Best place for runners and cyclists

Nicknamed “Track Town USA,” Eugene is considered a de facto capital of track and field, and it hosts numerous running events, particularly in the summer. It’s also a great place for more casual joggers, with numerous trails and a mix of hilly and flat terrain. Cyclists will find that the college city’s numerous bike lanes – including the Ruth Bascom Riverbank Trail System, which runs through sprawling Alton Baker Park – make it easy to get around town on two wheels.

5. The Willamette Valley

Best place for wine lovers

You don’t need to venture to France or Italy — or even to California’s Napa Valley — to immerse yourself in all things viticulture. Oregon’s Willamette Valley is among the best places to go wine tasting in the country. This region, which runs from just south of Portland all the way to Eugene, has all the trappings of a postcard-perfect wine destination, complete with rolling hills covered with vine plantings, lovely bistros, and loads of comfy-cozy bed and breakfasts. Best of all, tasting fees tend to be a little lower than in some other parts of the country, and are typically waived if you buy a couple of bottles or more. If you're thinking about a trip to Willamette Valley, check out our first timer's guide to the region.

Planning tip: Visit in the late summer for great weather and to see grapes on the vines. If you do end up coming during the harvest season (usually in September and October) expect some delays due to slow-moving farm equipment on country roads.

6. Bend

Best place for all-weather adventurers

The Central Oregon city of Bend is a magnet for outdoorsy folk, and its position east of the Cascade Mountains means that the climate is a bit drier and sunnier than what you’ll find in the western reaches of the state. Bend draws in skiers and snowboarders in the winter due to its proximity to Mt Bachelor, but it’s a particularly great base for summertime adventures. Popular activities range from rafting the Deschutes River to setting off on backpacking adventures in the Three Sisters Wilderness. Bend is also just a short drive from Smith Rock, one of the top destinations in the state for rock climbing.

Time your visit to Oregon just right with our seasonal guide

7. Crater Lake National Park

Best place for lake lovers

Protecting the deepest lake in the country, Crater Lake National Park is the only national park in Oregon. It's worth taking a boat ride out to Wizard Island, a cinder cone islet in the center of the caldera, and going for a spin along Rim Drive, a 33-mile loop that offers motorists (and cyclists) the chance to see Crater Lake from every angle. For particularly great views of the lake and the woods that surround us, take the 3.4-mile hike up to the top of Garfield Peak, accessible via a trailhead at the park's Rim Village.

Planning tip: Crater Lake National Park is incredibly popular, and campsites and lodging at the park fill up well in advance, so book as early as you can. If you can’t secure a spot, nearby Diamond Lake is a good alternative and is within an easy drive of the national park.

8. Ashland

Best place for theater fans

A short drive from the California border, the Southern Oregon city of Ashland’s biggest claim to fame is the Oregon Shakespeare Festival, a theater company that’s been presenting the works of the Bard himself since launching back in 1935. The season lasts for most of the year, taking a break in the cooler winter months, and features a solid annual lineup of Shakespeare’s classics along with a smattering of plays from other playwrights. For more of the best things to do in Ashland, check out our guide to this fun city.