Best Weekend Getaways in Oregon: 12 Places Worth the Trip
If you’re looking for the best weekend getaways in Oregon, the good news is that you have an almost ridiculous number of choices. Oregon manages to pack beaches, mountains, waterfalls, wine country, high desert, forests, quirky roadside attractions and cities with excellent food into one state. The bad news is that Oregon is not exactly tiny, so choosing a destination matters if you only have two or three days.
I’ve spent a lot of time exploring Oregon, including multiple trips to places like Bend, Sunriver, Newport, Cannon Beach, Hood River, Portland and Southern Oregon. I’ve also driven some seriously scenic routes through the state, chased waterfalls, gone off-roading, explored Crater Lake and put together a nine-day Southern Oregon road trip. In other words, I’ve learned that trying to see all of Oregon in one weekend is a terrible idea unless your idea of relaxing involves driving for six hours and saying, “Quick! Everybody out. We have 17 minutes here.”
So, I’ve broken down the best weekend trips in Oregon based on what you actually want to do. Whether you’re traveling with kids, looking for a romantic escape, planning a girls’ trip or just need to get out of town, there’s an Oregon getaway here for you.
Table of Contents
Best Weekend Getaways in Oregon at a Glance
If you don’t want to read the entire article before deciding where to go, here’s the short version:
- Best overall: Bend and Sunriver
- Best Oregon Coast getaway: Cannon Beach
- Best for families: Newport
- Best for waterfalls and scenery: Hood River and the Columbia River Gorge
- Best wine getaway: Willamette Valley
- Best city weekend: Portland
- Best family-friendly city getaway: Eugene
- Best mountain escape: Mt. Hood and Government Camp
- Best for a long weekend: Crater Lake
- Best road trip: Southern Oregon
- Best unique Oregon experience: Southern Oregon Coast
- Best for something completely different: Eastern Oregon and Silvies Valley Ranch
1. Bend and Sunriver: Best Overall Weekend Getaway in Oregon
If a friend asked me where they should go for their first Oregon weekend getaway, Bend and Sunriver would be near the top of my list. This area gives you the combination that makes a weekend trip work: plenty of things to do, good restaurants, outdoor activities and enough variety that everyone in the family can find something they actually enjoy.
I’ve spent enough time in Bend and Sunriver to have an entire Sunriver & Bend Travel Guide on MommyTravels. The area works year-round, with hiking, biking, kayaking, rafting, and horseback riding in warmer months and skiing, snowshoeing, and ice skating in winter. Sunriver is just south of Bend, so it’s easy to combine the two rather than choosing one and pretending you aren’t going to wander over to the other anyway.
One of the things I particularly like about this area for families is the sheer number of activities. We went whitewater rafting on the Big Eddy with Sun Country Tours, explored the High Desert Museum, went kayaking, and even did off-roading in the Bend/Sunriver area with Polaris Adventures. That last one is particularly fun if your family has reached the age where a normal sightseeing drive earns you eye rolls.
For lodging, I’ve stayed in several places around Bend and Sunriver, including Tetherow Lodge, SpringHill Suites Bend and a vacation rental in Sunriver. A vacation rental can be especially convenient for families because you get more space and a kitchen, which means you can occasionally avoid taking everyone to a restaurant when they’re already tired and hungry. That’s when parenting gets really exciting.
Best for: Families, outdoor enthusiasts, active couples, and anyone who wants lots of choices.
How long: Two or three nights.
Don’t miss: High Desert Museum, rafting, hiking, kayaking, and exploring both Bend and Sunriver.
2. Cannon Beach: Best Oregon Coast Weekend Getaway
There are a lot of places along the Oregon Coast, but Cannon Beach is the one I would recommend if you want that classic Oregon Coast experience. Haystack Rock gives you the instantly recognizable scenery, while the town has shops, restaurants and plenty of places to stay within easy reach of the beach.
I’ve been to Cannon Beach numerous times, and I finally found a hotel there that I really liked: Surfsand Resort. During one visit, we stayed in a two-bedroom suite that could accommodate a group of five or six, and the property sits right on the beach with views toward Haystack Rock. For families, that combination of space and beach access is hard to beat.
Cannon Beach is also a good destination if you don’t want to spend your entire weekend running from attraction to attraction. Walk the beach, explore around Haystack Rock when conditions allow, browse downtown and head to Ecola State Park for more of that dramatic coastline. In fact, Ecola is one of my favorite beaches in Oregon, so this is one of those destinations where I recommend leaving some empty space on your itinerary.
If you’re trying to keep the trip affordable, consider traveling during the week or looking for accommodations with kitchens. I’ve written about Cannon Beach as a budget-friendly summer destination before, and having a kitchen can make a noticeable difference when coastal lodging prices start doing their coastal-luxury thing.
Best for: Couples, families, beach lovers and first-time Oregon Coast visitors.
How long: Two nights.
Don’t miss: Haystack Rock and Ecola State Park.
3. Newport: Best Oregon Coast Getaway for Families
If you’re taking the kids to the Oregon Coast, Newport is one of my favorite choices because there is more to do than simply hope everybody enjoys staring at the ocean.
We’ve visited Newport multiple times, including for spring break, and I’ve put together a complete Newport, Oregon Travel Guide based on those trips. The Oregon Coast Aquarium, Yaquina Head, Devil’s Punchbowl, the sea lions and the Newport waterfront give families plenty of options.
The Oregon Coast Aquarium is particularly useful when you’re traveling with children because it gives you something to do when everyone has had enough wind blowing sand into their faces. Yaquina Head is another worthwhile stop, especially if you time your visit around the tide pools.
Newport also works well as a base for exploring other parts of the central coast. You can head north toward Lincoln City or south toward Yachats and Cape Perpetua, depending on how ambitious you feel.
Best for: Families, marine-life lovers and anyone who wants more activities than a typical beach weekend.
How long: Two or three nights.
Don’t miss: Oregon Coast Aquarium, Yaquina Head and the Newport Bayfront.
Read my Newport Oregon Travel Guide
4. Hood River and the Columbia River Gorge: Best for Waterfalls and Scenery
If your idea of a great weekend involves waterfalls, scenic drives, wineries, breweries and mountain views, Hood River is a fantastic choice.
I’ve written quite a bit about this area because there is an almost absurd amount to see. The Columbia River Gorge is packed with waterfalls, including Multnomah Falls, Horsetail Falls, Bridal Veil Falls, and Latourell Falls. My Mount Hood Scenic Loop guide combines several of these sights with Hood River and the drive toward Mt. Hood, making it a particularly good option if you want a weekend road trip rather than sitting in one town.
Hood River is also surprisingly good for families. I’ve visited several kid-friendly wineries in the area, and I specifically look for wineries with games, lawns or other things to keep children occupied while the adults get to enjoy a glass of wine. Because apparently children don’t appreciate the importance of terroir.
Hood River is also known for windsurfing and kiteboarding, and the area has plenty of opportunities for kayaking, paddleboarding and hiking. If you want a relaxing place to stay, I’ve also reviewed The Society Hotel Bingen, where we stayed in one of the two-bedroom cabins and really enjoyed having the extra space and peaceful surroundings.
Best for: Outdoor lovers, couples, families with older kids, wine lovers and photographers.
How long: Two nights.
Don’t miss: Columbia River Gorge waterfalls, Hood River and the Mount Hood Scenic Loop.
Read my Mount Hood Scenic Loop guide
Read my guide to kid-friendly wineries in Hood River
5. Willamette Valley: Best Oregon Wine Weekend
For a weekend where the main goal is relaxing, eating well and drinking good wine, Willamette Valley is an easy choice.
I’ve written about Willamette Valley as Oregon’s answer to Napa, but with fewer crowds and more flannel, and honestly, that pretty much sums up the appeal. The region has an enormous number of wineries, and towns such as McMinnville make good bases because you can combine wine tasting with restaurants, shops and a walkable downtown. A fun unique place to stay is Vintage Trailer Resort in Oregon’s Wine Country
One thing I appreciate about Oregon wine country is that you don’t necessarily have to make the trip adults-only. I’ve also covered kid-friendly wineries in the Willamette Valley, because sometimes getting a babysitter is less realistic than the fantasy version of your vacation where you magically have one.
If you are traveling with kids, look for wineries that have outdoor space, games, or other activities. If you’re traveling with friends or as a couple, you can make wine tasting the main event and let someone else handle the driving. This is one weekend where having a designated driver is a very good idea.
Best for: Couples, girlfriends’ getaways, wine lovers and food lovers.
How long: Two nights.
Don’t miss: McMinnville and the surrounding Willamette Valley wineries.
6. Portland: Best City Weekend in Oregon
Portland is the obvious choice if you want an Oregon weekend getaway without spending the entire weekend driving. You can eat, shop, visit gardens and museums, hike, and then be back at your hotel in time for dinner.
I’ve spent enough time in Portland to have multiple articles about the city and the surrounding area. One of the things I like most is that you can combine Portland with a day trip rather easily. Head east toward the Columbia River Gorge or south toward some of the area’s hiking trails, then return to the city for dinner.
For a hotel recommendation based on my own experience, I’ve stayed at The Porter in downtown Portland and particularly liked the room amenities, power outlets, and those ridiculously comfortable Frette robes. Eden and I actually voted them among the best hotel robes we’d experienced, which is an oddly specific category but apparently one we now take seriously.
Portland also has attractions such as the Lan Su Chinese Garden and Hoyt Arboretum, which means you can build a weekend that isn’t entirely centered around eating. Although I’m not going to pretend eating isn’t one of the city’s attractions.
Best for: Couples, girlfriends’ trips, food lovers, and travelers who like cities.
How long: Two or three nights.
Don’t miss: Washington Park, Hoyt Arboretum, Lan Su Chinese Garden and Portland’s food scene.
7. Eugene: Best Underrated Family Weekend
Eugene doesn’t always make the list of Oregon’s most famous destinations, but it should if you’re traveling with kids. I’ve found myself there repeatedly for Noah’s gymnastics meets, and each visit has given me another reason to like the city.
Eugene is less than two hours south of Portland and has a surprisingly long list of family-friendly things to do. Skinner Butte Park has a large playground and bike paths, while the Cascades Raptor Center, Science Factory, Level Up Arcade and Get Air Eugene Trampoline Park provide options for different ages and weather conditions.
The city also happens to be home to the University of Oregon, so if you have a sports fan in the family, checking the Ducks’ schedule can add another activity to the weekend. I’ve also found several family-friendly restaurants here, including Track Town Pizza, McMenamins East 19th Street Cafe and Sweetwaters on the River.
Best for: Families, sports fans and people looking for a less obvious Oregon getaway.
How long: Two nights.
Don’t miss: Skinner Butte Park, Cascades Raptor Center and the University of Oregon.
Read my 12 Family-Friendly Things to Do in Eugene
8. Mt. Hood and Government Camp: Best Mountain Getaway
If you want to trade city streets for mountain air, Mt. Hood makes an excellent Oregon weekend getaway. The area works in both summer and winter, which is convenient because Oregon apparently didn’t want to make choosing a season easy either.
Timberline Lodge is one of the area’s major attractions. The historic lodge was built from 1936 to 1938 as a Works Progress Administration project and sits on the south side of Mt. Hood.
You can also build a weekend around the mountain itself, Government Camp, and the surrounding scenic drives. Winter is the obvious choice for skiing and snow activities, while summer brings hiking and other outdoor recreation.
Best for: Couples, outdoor enthusiasts, skiers and families with older children.
How long: Two nights.
Don’t miss: Timberline Lodge and the drive around Mt. Hood.
Read: Things to do on Mt. Hood and Mt. Hood Summer Getaway: Cooper Spur Mountain Resort
9. Crater Lake: Best Oregon Long Weekend
Crater Lake is not my pick for a casual two-night weekend from Portland. But if you have a long weekend and are willing to drive, it is absolutely worth considering.
I’ve visited Crater Lake many times since at one point we were stationed in Klamath Falls and it was nearby. One of the best ways to make the trip more worthwhile is to turn the drive itself into part of the experience rather than treating it as nothing more than a way to get from point A to point B.
Toketee Falls is one of the stops I recommend near Crater Lake, and the Rogue-Umpqua Scenic Byway is another excellent option. The 172-mile route passes through Crater Lake, Diamond Lake and Umpqua National Forest, with waterfalls and other scenic stops along the way.
Just pay attention to seasonal road conditions before you go. On one of my Southern Oregon trips, winter weather caused closures around Crater Lake that significantly changed the drive. Oregon’s mountains do not care that you made a three-day itinerary in a Google Doc.
Best for: Nature lovers, road trippers and anyone wanting a spectacular long weekend.
How long: Three or four days is better than two.
Don’t miss: Crater Lake, Toketee Falls and the Rogue-Umpqua Scenic Byway.
Read 11 Things to Do Near Crater Lake
10. Southern Oregon: Best Oregon Road Trip
If you have three or four days rather than just one weekend, Southern Oregon is where I would start looking. I’ve actually put together a nine-day Southern Oregon road trip that includes waterfalls, Crater Lake, Klamath Falls, ziplining, Oregon Caves, a treehouse resort, redwoods and the Oregon Coast.
Obviously, you’re not going to duplicate that entire itinerary in a weekend. Instead, pick one section and slow down. The Umpqua area is excellent for waterfalls, with Toketee Falls, Clearwater Falls, Fall Creek Falls, Whitehorse Falls and Watson Falls all accessible along the scenic Highway 138 corridor.
Another option is to focus on the Grants Pass and Oregon Caves area. The Oregon Caves are a completely different experience from the coast or mountains, and the Out ‘n’ About Treehouse Treesort gives families an opportunity to stay somewhere considerably more memorable than a standard hotel room.
And if you really want to make the weekend interesting, head toward Bandon and the Southern Oregon Coast. My longer road trip included windsurfing or kiteboarding at Floras Lake, Bandon Beach horseback riding and Bandon Dunes. That’s a lot for a weekend, but you can easily choose one or two experiences and make them the centerpiece of the trip.
Best for: Families with older kids, adventurous travelers and road-trip lovers.
How long: Three to five days is ideal.
Don’t miss: Umpqua waterfalls, Oregon Caves, Crater Lake or Bandon, depending on your route.
Read my Ultimate Southern Oregon Road Trip
11. Yachats and the Central/Southern Oregon Coast: Best for Something Weird
If you’ve already done Cannon Beach and Newport and want to see a different side of the Oregon Coast, head farther south.
One of the places I’ve covered is Thor’s Well near Yachats, a dramatic coastal formation that looks like the Pacific is disappearing into a hole in the ground. It is exactly the sort of Oregon attraction that makes you stop and wonder who looked at it and thought, “Yes, let’s stand near that.”
The Central and Southern Coast also give you access to places like Cape Perpetua, Harts Cove and other rugged coastal landscapes. This is a better choice for travelers who want scenery and hiking rather than a traditional beach-town weekend.
Just use common sense around coastal hazards. Thor’s Well and other rocky coastal areas can be dangerous, particularly during rough surf, and the ocean does not care how good your Instagram shot is going to be.
Best for: Couples, hikers, photographers and adventurous travelers.
How long: Two or three nights.
Don’t miss: Yachats, Thor’s Well and Cape Perpetua.
See my Unique Places to Visit in Oregon
12. Silvies Valley Ranch: Best Luxury Escape in Eastern Oregon
If you’re looking for something completely different, Silvies Valley Ranch in Eastern Oregon deserves consideration. This isn’t your typical Oregon Coast weekend or mountain getaway. It’s a luxury dude ranch where you can combine outdoor activities with comfortable accommodations, food, and spa time.
Silvies Valley Ranch is one of those places that feels like its own destination. Activities can include horseback riding and other ranch experiences, while the property also has a spa, dining and luxury cabins. They also have a ton of golfing, including a reversible golf course. We had a goat caddy when we did their nine par.
This is particularly appealing for a couples’ getaway, girlfriends’ trip, or family trip where you want everyone to have things to do without spending your entire vacation driving between them.
Best for: Luxury travelers, couples, families and girlfriends’ getaways.
How long: Two or three nights.
Don’t miss: The ranch activities, spa and luxury cabins.
Read my Silvies Valley Ranch review
How to Choose the Best Oregon Weekend Getaway
The easiest way to choose an Oregon weekend getaway is to decide what kind of trip you actually want before you pick the destination. Otherwise, you’re going to end up with a very ambitious map and a vacation that consists primarily of windshield views.
If you want outdoor adventure, choose Bend and Sunriver. If you want a classic beach weekend, head to Cannon Beach. For a family beach trip with lots of activities, Newport is a better bet. If you’re looking for waterfalls, wineries and scenery, Hood River and the Columbia River Gorge are hard to beat.
For wine tasting, head to Willamette Valley. For a city weekend, choose Portland. If you’re traveling with kids and want a city that has plenty of family activities without the intensity of Portland, give Eugene a look.
For a mountain escape, choose Mt. Hood. If you have a long weekend and want one of Oregon’s biggest natural attractions, head to Crater Lake. And if you’re willing to turn the weekend into a road trip, Southern Oregon gives you an incredible amount to work with.
When Is the Best Time to Visit Oregon for a Weekend Getaway?
That depends heavily on where you’re going. Summer is the easiest season for an Oregon Coast trip, mountain activities and many outdoor adventures, but it is also when popular destinations can be busiest.
Fall can be particularly appealing for wine country and parts of Central Oregon, while winter is a good time to head toward Mt. Hood and Bend for snow activities. Spring brings waterfalls, greenery and wildflowers, although mountain roads and higher-elevation destinations can still have winter conditions.
One of the reasons I like Oregon so much is that there isn’t really one “best” time to visit the entire state. There are simply different versions of Oregon depending on the season.
How Many Days Do You Need for an Oregon Weekend Getaway?
For most of the destinations on this list, two nights is enough for a good weekend trip. Bend, Cannon Beach, Newport, Hood River, Eugene, Portland, and Willamette Valley can all work well with a Friday-to-Sunday schedule.
Crater Lake and Southern Oregon are different. If you’re traveling a long distance to reach them, I’d give yourself at least three nights so you’re not spending half your vacation driving. My Southern Oregon road trip is nine days for a reason: there is a lot to do and see.
And that’s really the biggest piece of advice I can give you when planning an Oregon getaway: don’t try to see everything at once. Oregon has enough waterfalls, beaches, mountains, wineries, and weird roadside attractions to keep you coming back for years.
I’ve been traveling around Oregon for years and still have places I haven’t explored. That’s actually a pretty good problem to have.
Final Thoughts on the Best Weekend Getaways in Oregon
Oregon is one of the best states for a weekend getaway because you can have a completely different experience depending on which direction you drive. You could spend one weekend watching the waves crash around Haystack Rock, another hiking around Bend, another drinking wine in Willamette Valley and another chasing waterfalls through Southern Oregon.
And if you’re planning a family trip, don’t assume the kids need a giant attraction to have fun. Some of our best Oregon experiences have been things like rafting, off-roading, exploring waterfalls, playing at parks, and simply getting outside together. The goal isn’t to check every attraction off a list. It’s to come home with a trip everyone actually enjoyed.
So pick the part of Oregon that fits your travel style, book the trip and leave a little room for the unexpected.
