Pacific Northwesterner’s Guide to 12 Perfect Destinations in Oregon for a Weekend Trip
A bonus perk of living in Washington is the fact that I’m now just a drive away from some of the most beautiful places in Oregon, many of which make for fabulous weekend getaways. Even if it’s too far to drive, you can easily fly into one of the smaller airports of Oregon, like Eugene Airport or Rogue Valley International Medford Airport.
When you think about taking a weekend getaway in Oregon, a trip to or near Portland may first come to mind. But there’s so much more to this Pacific Northwestern state than its largest city – from the mountains to vineyards to the coast, you’ll find plenty of worthy destinations for an epic weekend getaway in Oregon. So in this article I’ll be covering 12 awesome weekend trips, all around Oregon, including (of course!) Portland.
Each of the trip ideas below are perfect for a weekend. These Oregon locales are not so large that they’ll overwhelm you, but there are still enough things to do at each of these destinations to build a jam-packed trip itinerary.
One more thing before we get to our top 12 list: When visiting Oregon for the weekend, keep the seasonal weather in mind. In Western Oregon, it rains frequently throughout the winter, but you likely won’t see snow. If you go to Eastern Oregon, though, winter brings colder temperatures and a great deal of snow. Due to the precipitation, trails and hiking paths may be muddy, icy, or even closed off in the winter and spring. If hiking is on your to-do list, consider visiting over the summer. Inland Southern Oregon can get extremely hot in the summer months and often has a fire season in late summer/early autumn to be cognizant of if traveling during that time.
Alright, now to the top 12 weekend getaways in Oregon! Starting with…
Ashland: Shakespeare and Hipster Vibes in South Central Oregon
Ashland is like a mini Portland with a (big) dash of Shakespeare. Known for it’s 9-month long Shakespeare Festival, which features a variety of plays and performances beyond Shakespeare’s repertoire, Ashland has a prominent arts scene, but offers much more than that.
Main Street is lined by a variety of shops and mercantiles, many of which have a local flair. Don’t miss out on the collection of Paddington shops (Paddington Station, Paddington Jewel Box, and Inspired by Oregon), with each store offering a different mix of kitsch and modern products. I also especially like the Drift Collective, which features arts, jewelry, and other wares by local artisans, plus a little bar in the back that serves up local drinks like craft beer, kombucha, and hard seltzer. Also, if you’re traveling to Ashland with kids, the bright and well-stocked Bugg’s Toys is sure to delight.
For eats, don’t miss dining along the scenic creek that runs below Main Street and into scenic Lithia Park. And speaking of water, don’t miss learning about Ashland’s famed Lithia water, which you can even taste at the fountains downtown.
Where to Stay in Ashland
Ashland Springs Hotel: Historic inn located right along Main Street.
Tillamook: Cheese Tasting and Kayaking Near the Coast
Dairy lovers should head to Tillamook, home to Tillamook Creamery. There, you can watch cheese get made in real time and sample some of the company’s delicious ice cream (I love the marionberry!). Blue Heron Cheese Company is another fun place to go cheese tasting, plus they have wine tasting and farm animals onsite.
You can also see planes, blimps, and World War II memorabilia at the Tillamook Air Museum.
Like most other Oregon cities, Tillamook has hiking trails for those seeking outdoor activities. Kayaking is also a surprising excursion not many people know about in Tillamook. Since its close to lakes, rivers, and sea bays, there are several different type of kayaking options. (Check out Kayak Tillamook for guided tours.)
Tillamook is 90 minutes away from Portland and a half hour away from Pacific City on the coast. Summer tourists may want to visit the Oregon Coast and Tillamook at the same time. If you choose to do this, you’ll likely still have time to explore Tillamook during your weekend trip.
Where to Stay in Tillamook
Netart’s Surf Inn: This is a small motel near the coast with colorful, beachy rooms.
Tillamook also has many vacation rentals, which you can browse through here.
Corvallis: Family Fun in a Western Oregon Inland College Town
This college town is relatively quiet, yet there’s plenty to do. For those seeking a laid-back destination that won’t leave you bored, Corvallis is a great choice for a weekend getaway in Oregon.
If you’re visiting with your friends and family, play a round at Escape Corvallis, an escape room attraction with levels suited for everyone. Other indoor activities include Highland Bowl and Valley Rock Gym, perfect for when it’s too rainy to visit the town’s 2,000 acres of parks.
Visiting beer lovers should definitely check out the breweries in Corvallis – Block 15 and 2 Towns Ciderhouse both have tasting rooms in town. Corvallis also borders the South Willamette Valley and is close to a number of renowned wineries and tasting rooms.
Corvallis is an hour and half south of Portland, an hour away from Newport (on the coast), and 45 minutes away from the state capital.
Where to Stay in Corvallis
To stay near the university, the Hilton Garden Inn is a good option. For easy downtown access, check out the hip Hotel Corvallis or the river-adjacent Courtyard by Marriott Corvallis. Or book the lovely Holiday Inn Express Corvallis-on the River hotel on the edge of downtown to be right by the water.
If you’re looking for lodging in an area of Corvallis without as much nighttime activity, consider staying at Best Western or Comfort Suites in northern Corvallis. These hotels aren’t right by the campus and downtown, yet those locations are still a short drive away.
Sisters, Central Oregon
Located in Central Oregon, this tourist town is a great getaway spot no matter if it’s snowy or sunny.
If you’re visiting during the winter, head to Hoodoo Ski Area for skiing, lessons, and a snow tubing park. Sisters is so great in winter that I wrote a whole article about it! Click here for the top winter things to do in Sisters.
Travelers arriving in the summer can hike to Koosah and Sahalie Falls, Canyon Creek Meadows, and Proxy Falls.
Sisters is a half hour away from it’s more famous little Oregon city, Bend, another fun trip destination. Due to its proximity, it would be easy to include Bend in your weekend trip itinerary, too, so we’ve included in next in this list.
Where to Stay in Sisters
For an unforgettable weekend getaway, stay in one of the cottages at the luxurious FivePine Lodge in Sisters. Each cottage even has a waterfall soaking tub and gas fireplace! Black Butte Ranch is also a great place to stay for golfing and resort ambiance.
Bend, Central Oregon
Are you looking for the last remaining Blockbuster? Look no further than Bend, Oregon. (Ok, Bend is much more than just a historic video store, but I think that’s pretty fun.) This Central Oregon town is also home to epic hiking trails, water sports, and ski slopes.
Hikers should check out Tumalo Falls, the Newberry National Volcanic Monument, and the Oregon Badlands Wilderness Area. If you’re visiting when there’s snow on the ground, grab some ski lift tickets to Mt. Bachelor. Adventure seekers will enjoy whitewater rafting down the rapids of Deschutes River or tubing down gentler parts of the river. No matter when you visit Bend, there will always be fun things to do here – especially outside.
Bend is three and a half hours away from Portland. If you’re short on time and don’t want to waste it driving, look into flying to Bend’s regional airport instead of Portland; Robert’s Field Airport sits right outside of Bend and there are direct flights from Seattle, Denver, and Salt Lake City.
Where to Stay in Bend
Check out the Oxford Hotel to be in downtown or the Riverhouse on the Deschutes to be closer to Bend’s river scenery.
Crater Lake, Southeast Oregon
Crater Lake National Park in Southern Oregon is Oregon’s only national park. The result of a volcanic eruption that sunk the volcano and formed a caldera, eventually filling up with water. Today, it offers crystal-clear waters that you can view from Rim Drive. Take a shuttle from the park to Wizard Island, a cinder cone within Crater Lake that’s suitable for swimming and hiking. Alternatively, climb up Mount Scott Trail to get the best views of the park.
Crater Lake is four hours south of Portland and about 90 minutes from Medford, which I recommend using as your base for visiting Crater Lake.
Where to Stay for Crater Lake
You can make reservations at Crater Lake’s lodges up to a year in advance, so you should make them as soon as you know you’ll be visiting. They book up fast! The small city of Medford is also a great place to base yourself for a visit to Crater Lake. I had a very pleasant stay at Compass by Margaritaville hotel in Medford.
––> Read More: The Perfect Day Trip to Crater Lake From Medford, Oregon
McMinnville, Weekend Getaway in Oregon’s Wine Country
This Oregon town is known for its vineyards, art galleries, and other cultural activities. McMinnville is surrounded by the Willamette Valley and its rolling acres of vineyards and famous Pinot Noir wines. In addition to tasting rooms located in the valley, Willamette has many tasting rooms right in town within walking distance to each other.
Those visiting Oregon with kids should go to the Wings & Waves Waterpark, an indoor attraction with an impressive aviation museum attached to it.
McMinnville is an hour away from Portland, nearly two hours from Seaside, and a half hour away from Salem, the state’s capital.
Where to Stay in McMinnville
We loved our stay at 3rd Street Flats. The colorful, spacious apartments are right in the center of town and walking distance to tasting rooms and restaurants.
Seaside, Northwest Coast of Oregon
The Oregon Coast is always a good vacation spot for summer travelers. And thanks to Seaside, you don’t need to go to California to experience West Coast waves and boardwalks! This beach town’s promenade is lined with shops, nightlife, and other attractions worth visiting when you’re not in the water. Families walking down the “prom” should also make time to visit the Seaside Aquarium’s seals and crustaceans.
With a couple surfing schools located in Seaside, avid ocean enthusiasts can even learn to surf in Seaside. Just bring or be ready to rent a wetsuit — the water is cold along the coast of Oregon!
Where to Stay in Seaside
I highly recommend the oceanview suites overlooking the promenade and coast at the Seaside Oceanfront Inn. We stayed in the Deluxe Suite with Oceanview and it was so dreamy with the views and loft and sunken bathtub. Delicious room service from the adjacent Maggie’s on the Prom restaurant, too!
Cannon Beach, Oregon’s Northern Coast
Unlike other coastal regions, not every town on the Oregon Coast is the same! Cannon Beach is a short drive from Seaside, but has a very different vibe. The downtown area is more boutique-y and upscale feeling than Seaside while still incorporating in the incredible nature around the town.
I like to think of Cannon Beach as the Hamptons of the Pacific Northwest.
In addition to shops and restaurants, the coastline of Cannon Beach is home to Haystack Rock, an iconic landmark featured in Kindergarten Cop and The Goonies.
Ecola State Park and Oswald West State Park are also both located by Cannon Beach, each boasting hiking trails for every fitness level. If you’re looking to spend a weekend immersed in nature with some excellent meals and drinks, a weekend trip to Cannon Beach may be just what you need.
Cannon Beach sits 15 minutes south of Seaside and an hour and a half outside of Portland.
Where to Stay in Cannon Beach
There are plenty of waterfront hotels in town if you’re in need of lodging, as well as vacation rentals. If you’re traveling without kids, be sure to check out the famous Stephanie Inn for your lodging (kids under 12 aren’t allowed; it’s a great spot for a romantic getaway in Oregon). Families will enjoy Hallmark Resort Cannon Beach.
Salem, Western Oregon Inland
As the capital of Oregon, there are many reasons to visit Salem. Families will find kid-friendly attractions like the Riverfront Carousel, the Enchanted Forest amusement park (20 minutes away), and the Gilbert House Children’s Museum.
Tourists who are interested in Oregon’s history and politics should add the Willamette Heritage Center and a capitol building tour to their trip itineraries.
Salem is 50 minutes away from Portland, about two hours away from Seaside, and 45 minutes away from Corvallis.
Where to Stay in Salem
The Grand Hotel is a beautiful hotel centrally located in downtown Salem within walking distance to the state capitol.
Eugene, Western Oregon Inland
Like Corvallis, Eugene is a college town in the Willamette Valley. However, Eugene is a bit busier since it’s the second largest city in Oregon.
The University of Oregon has several attractions on campus, like the Museum of Natural and Cultural History and the Jordan Schnitzer Museum of Art. If you time your trip right, you can catch a show at the Cuthbert Amphitheater – otherwise, check out the Hult Center for Performing Arts’ schedule.
Eugene is an hour and 45 minutes away from Portland, an hour south of Salem, and three hours away from Seaside.
Where to Stay in Eugene
The swanky Inn at the 5th and the artsy Gordon Hotel are two hotels in downtown Eugene that offer upscale amenities. If you don’t care about staying downtown, check out the Valley River Inn on the other side of the Willamette River.
Pro Tip: If you’re booking a hotel in this city, make sure you’re not visiting when college students move into their dorms or graduate. Otherwise, you’ll be competing with parents for lodging and it may be much more expensive.
Getaway on an Amazing Weekend in Oregon!
Oregon is filled with exciting places to spend your weekend, no matter what you’re looking to do during your trip. From small cities to beach paradises, you’ll find it all in this uniquely beautiful and exciting state.