The Best Vacation Destinations in Oregon

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Oregon’s wild west past attracts millions of adventurers every year—it’s much easier these days to blaze your own Oregon Trail (no covered wagon necessary!)

With charming little beach towns, exciting cities, and stunning remote areas of natural beauty, Oregon has something for every type of vacationer.

Many of the best vacation spots in Oregon are accessible by bus or train, so you can easily travel between cities and even to the state’s more remote areas of natural beauty.

Here are our picks for the best places to vacation in Oregon to help you plan an unforgettable getaway.

1. Crater Lake National Park

Southern Oregon is where you’ll find Crater Lake National Park and the deepest lake in the United States. Enjoy hiking, swimming, and fishing at this pristine lake formed thousands of years ago when the volcano collapsed. The scenery alone makes Crater Lake one of the best places to visit in the Western United States.

Campers will love roughing it here or stay at the park’s cozy lodge. Try the dining room for yummy meals created with locally sourced ingredients!

Be sure to take a boat tour to Wizard Island, the 763-foot cinder cone in the center of the lake. Then, hike the Wizard Island Summit Trail, the path leading to the crater at the top of the island.

From late June until early October, you can take the Crater Lake Trolley from the train station in Klamath Falls right to the park’s Rim Village.

Book Your Trip:

Bus & train prices are based on the average cost of a one-way ticket for the respective route available on Wanderu over a 30-day period. 

2. Cannon Beach

Dreaming of sandy toes and a sun-kissed nose? The small city of Cannon Beach features miles of sandy beaches perfect for a relaxing summer getaway on the northern Oregon coast.

Drink in the area’s dramatic scenery, provided by shoreline rock formations like Haystack Rock. Be sure to venture out to Hug Point (just a short ride from downtown) for its pretty waterfall and sandstone caves.

Nearby Ecola State Park is the perfect day trip from Cannon Beach, with year-round activities for all kinds of adventurers. Hiking trails, picnic spots, and miles of scenic shoreline ensure you’ll snap some epic vacation pics. There’s even a historic lighthouse!

Book Your Trip:

Bus & train prices are based on the average cost of a one-way ticket for the respective route available on Wanderu over a 30-day period. 

3. Portland

Known for being a hipster mecca, trendy Portland is one of the best places to visit in Oregon. Foodies love the city’s eclectic mix of independent restaurants (including lots of cheap, weird little spots), and there are endless epic things to do in Portland.

Spend an afternoon wandering Portland’s Japanese Garden with its twelve acres of bonsai and koi. Or channel your inner art-lover at the Portland Art Museum, the perfect escape from the city’s famous rain.

Portland’s also home to the world’s largest indie bookstore: Powell’s takes up an entire city block! Fun fact: Oregon is one of only five states with no sales tax, making shopping that much cheaper. To save even more, check out our guide to 15 Free Things You Can Do in Portland.

Plan your trip to Portland during the summer—June through August is the best time to go (and we bet you won’t want to leave!)

Book Your Trip:

Bus & train prices are based on the average cost of a one-way ticket for the respective route available on Wanderu over a 30-day period. 

4. Mount Hood National Forest

Home to the state’s tallest mountain (its peak is more than 11,000 feet above sea level!), Mount Hood National Forest is one of the best vacation spots in Oregon for outdoor activities.

Mount Hood is the world’s second most climbed peak in the world (Japan’s Mount Fuji takes the #1 spot), so seasoned climbers will want to check this iconic mountain off their list.

But this National Forest is also home to six ski areas. With snow cover at the peaks year-round, you’ll enjoy the longest ski season in North America— from November until May. Mount Hood Skibowl also offers the country’s most extensive night skiing terrain.

Summertime adventurers can enjoy kayaking and swimming at Trillium Lake, or hike Mt. Hood’s 39-mile Timberline Trail.

Book Your Trip:

Bus & train prices are based on the average cost of a one-way ticket for the respective route available on Wanderu over a 30-day period. 

5. Bend

The small city of Bend is Central Oregon’s best year-round vacation spot, with tons of outdoor recreation opportunities. Hiking in the summer, rock-climbing in spring or fall, and skiing or snowboarding in winter make this the perfect place for sporty adventurers. (Find out why Bend is one of the best vacation destinations for college students).

Nearby Deschutes National Forest offers hiking and mountain biking trails with unbeatable scenery—rugged mountains, wildflower meadows, and plunging waterfalls.

But a vacation in Bend isn’t just about outdoor activities—the city’s also home to a lively dining scene. You’ll discover thriving independently-owned restaurants and food carts, all offering delicious eats.

If you’re feeling thirsty, Bend has so many craft breweries that it’s earned the nicknames “Beer Town USA” and “Beervana.” Cheers! 🍺

Book Your Trip:

Bus & train prices are based on the average cost of a one-way ticket for the respective route available on Wanderu over a 30-day period. 

6. Columbia River Gorge

If stunning views are what you’re after, you’ll find them when you visit the Columbia River Gorge on Oregon’s northern border. Gaze with awe as the Columbia River cuts through the Cascades, spilling dozens of waterfalls from basalt cliffs. The famous Multnomah, Bridal Veil and Latourell Falls are all in this National Scenic Area.

The Gorge is an explorer’s dream — hike up Dog Mountain, bike around The Dalles, windsurf at Hood River, or simply enjoy the wildflowers at Rowena Crest — the choice is yours!

Or explore the area’s fantastic wineries, where you’ll find a variety of wines, thanks to the Gorge’s unique geography. The hilly, cooler western part of the Gorge is perfect for growing pinot noir and chardonnay. The dry and sunny eastern vineyards feature syrah and tempranillo.

The Gorge’s scenic area encompasses several cities and towns along the Columbia River, but we recommend making Hood River your homebase, from which to explore the area’s waterfalls and wineries.

Book Your Trip:

Bus & train prices are based on the average cost of a one-way ticket for the respective route available on Wanderu over a 30-day period. 

7. Astoria

This small Oregon port city at the mouth of the Columbia River is the state’s oldest city and one of the best romantic getaways in Oregon.

One of Astoria’s most famous landmarks, the Astoria Column, is a 600-foot tall tower featuring a spiral staircase leading to an observation deck— don’t miss its spectacular city views! The column’s colorful murals highlight Oregon’s history, including the end of the Lewis and Clark expedition (the explorers spent the winter in what’s now Astoria before heading back East).

Stroll hand-in-hand along the Astoria Riverwalk to discover various restaurants, museums, and breweries. History fans will love a ride on the 1913 trolley offering a historical narrative of the area, running from March until December.

Book Your Trip:

Bus & train prices are based on the average cost of a one-way ticket for the respective route available on Wanderu over a 30-day period. 

8. Eugene

Culture vultures will love a getaway to Eugene, Oregon’s third-largest city. It’s home to several historical and art institutions—don’t miss local favorite Hult Center for the Performing Arts for live music, dance, and events.

Enjoy Eugene’s plentiful green spaces, including Alton Baker Park and the Owen Rose Garden. Pro tip: visit in spring to see the roses in full bloom.

Outdoorsy types will love spending a day at the McKenzie River National Recreation Trail, a hiking and mountain biking destination leading to several waterfalls, including Sahalie and Koosah Falls. Follow the McKenzie River on this 26-mile trail past Clear Lake to find the Great Spring, the river’s source.

Book Your Trip:

Bus & train prices are based on the average cost of a one-way ticket for the respective route available on Wanderu over a 30-day period. 

9. Sisters

Want to experience Oregon’s wild west heritage during your vacation? The charming town of Sisters hosts folksy events like the Sisters Rodeo, Sisters Outdoor Quilt Show, and the Sisters Folk Festival.

Exploring Sisters’ downtown, with its classic 19th-century western-style buildings, will make you feel like you’ve stepped back in time. Wander its unique shops and art galleries to pick up a souvenir from your Oregon getaway.

Named for the nearby Three Sisters mountains, Sisters is also the perfect starting point for many outdoor activities! Opportunities for hiking, mountain biking, skiing, SUP, and golf are all nearby.

Book Your Trip:

Bus & train prices are based on the average cost of a one-way ticket for the respective route available on Wanderu over a 30-day period. 

10. Salem

There’s something for everyone in Oregon’s capital city, making Salem a great year-round destination for your Oregon vacation plans.

Check out the city’s wealth of museums, including the 19th-century Bush House Museum and Willamette University’s Hallie Ford Museum of Art.

Foodies will enjoy Salem’s impressive range of farm-to-table restaurants, and locals know to head to Word of Mouth Bistro for the biggest brunch food around. Or explore the Ale and Cider Trail to sample the best of the city’s local refreshments.

Get back to nature in the heart of the city at Bush’s Pasture Park, a 90-acre public green space and botanical garden with walking trails, picnic areas, and a massive garden featuring fruit orchards and over two thousand roses.

Book Your Trip:

Bus & train prices are based on the average cost of a one-way ticket for the respective route available on Wanderu over a 30-day period. 

11. Samuel H. Boardman State Scenic Corridor

One of Oregon’s best-kept secrets, a getaway to the Samuel H. Boardman State Scenic Corridor in the state’s southwest corner is one of the best vacation choices you can make.

Stretching twelve miles along the coast, the corridor is packed with beautiful scenery — Sitka spruce trees, majestic rock formations, and even sandy beaches dotted along the rugged coastline.

Experienced hikers wouldn’t want to miss exploring the 27 miles of the Oregon Coast Trail that wind through this area. This is a fairly difficult hike, but novice trekkers can find plenty of easier trails to enjoy the scenery.

Head to Brookings, OR to access this beautiful spot (and to find hotels or campgrounds to use as your home base for exploring).

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12. Seaside

The tiny coastal city of Seaside features one of Oregon’s most famous landmarks — the oceanfront ­Promenade and its famous 1920s automobile Turnaround. “The Prom” is Seaside’s best spot for a walk, leisurely bike ride, or just a bit of people-watching.

Just steps from the Prom is the Seaside Aquarium, a classic attraction that’s been a Seaside favorite for over 80 years. Kids at heart wouldn’t want to miss a visit to Captain Kid Amusement Park for mini-golf or a spin on the go-kart track.

Seaside is also one of the best places to vacation in Oregon because it’s close to so many of the state’s coastal attractions. Within just 15 miles of the city, visitors will find Lewis and Clark National Historical Park, Tillamook Head, and Ecola State Park.

Book Your Trip:

Bus & train prices are based on the average cost of a one-way ticket for the respective route available on Wanderu over a 30-day period. 

No matter what kind of trip you’re looking to take, you’ll find some of the best vacation destinations in Oregon. And if you want even more destinations to check out in the beautiful Pacific Northwest, check out our list of the absolute best vacation destinations in Washington State

When you’re ready for your adventure, you’ll find the cheapest bus and train tickets on Wanderu to save money on your Oregon vacation!

Travel Safely

At Wanderu, we want to make sure you are equipped with all the information you need to plan a safe trip. Please visit our COVID-19 Travel Guide for the latest tips & advisories.

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About the author
Carrie Ann Karstunen

Carrie Ann Karstunen

A lifelong adventurer, Carrie Ann is equally at home hiking atop a glacier in Alaska or snorkeling a Caribbean shipwreck. Carrie Ann is always on the lookout for hidden beaches, offbeat museums, and scenic trails in the places she explores.