13 Weekend Trips From Portland | Insider’s Guide on Best Spots
One of my favorite things about living near Oregon has been the weekend trips from Portland and how there is something to do for everyone.
Whether you want to spend the summer exploring the Oregon Coast, sip wine at a Willamette Valley vineyard in the spring, hike through colorful forests in the fall, or enjoy a cozy mountain retreat in the winter, Portland makes the perfect base for year-round adventures.
With so many incredible weekend getaway options from Portland, it can be tough to decide where to go.
In this guide, I’ll share how far each destination is from Portland, what makes it worth visiting, and the best activities to enjoy while you’re there.
My Favorite Travel Resources
– Best Hotel Rates: Booking.com
– Best Rental Cars: Rentalcars.com
– Best Tour Services: Viator
Weekend Trips From Portland
The 13 destinations below are ones where I’ve enjoyed everything from outdoor adventures to laid-back, relaxing weekends. Each spot offers its own unique vibe, local flavors, and activities to discover. Let’s dive in!
1. Painted Hills, John Day Fossil Beds National Monument
Distance from Portland: 4 hours
Why Visit? Located in Eastern Oregon, the Painted Hills are part of the breathtaking John Day Fossil Beds National Monument. These hills began to form 35 million years ago when pumice and ash from volcanic eruptions in the Cascade Mountains traveled east and sprinkled over this part of the land.
Activities:
- Walk one of the five Painted Hills trails
- Photography
- Swim in the John Day River
2. Mount Hood
Distance from Portland: 1 hour + 35 minutes
Why Visit? Mount Hood is hands down one of my favorite places in all of Oregon.
If you love hiking, skiing, snowboarding, or simply enjoying mountain views, this is the perfect spot for an adventure-filled weekend.
Activities:
- Skiing
- Hiking
- Cozy Cabin Rentals
- Backpacking (permit required)
3. Hood River
Distance from Portland: 1 hour + 10 minutes
Why Visit? Located along the Columbia River Gorge, Hood River is a laid-back spot that’s perfect for a weekend getaway. Whether you’re windsurfing on the river, picking fresh fruit at local orchards, or grabbing a drink at a cozy winery, this place has the perfect mix of outdoor fun and relaxing vibes.
Activities:
- Kitesurfing in the Columbia River
- Visit (my favorite) Stave and Stone Winery
- Mount Hood Railroad (book in advance!)
- Hike in the Columbia River Gorge
North Face Fuzzy Traction Slippers
Whether I’m backpacking, road-tripping, or traveling internationally, these slippers are the first thing I pack. With rubber traction soles and a cozy fit, these are perfect for apres-ski, lounging, or casual wear. They are durable, water-resistant, and feel like duvets on your feet.
4. Cannon Beach
Distance from Portland: 1 hour +30 minutes
Why Visit? The iconic Haystack Rock is one of the top places to visit in Oregon. Wide sandy shores and a cozy small-town vibe, it’s perfect for beach walks, browsing local shops, and soaking in the coastal views.
Activities:
- Walk the beaches
- Visit the small-town shops
- Oregon Coast Tour from Portland
5. Bend
Distance from Portland: 3 hours + 20 minutes
Why Visit? If you love the outdoors and chill vibes, Bend is the place for you, an outdoor enthusiast’s paradise.
Activities:
- Snowboarding at Mt. Bachelor
- Hiking & Biking Trails
- Oregon Outback Adventure ATV Tour
- Cascade Lakes Kayak Tour
- Deschutes River Horse Ride
6. Terrebonne
Distance from Portland: 2 hours + 45 minutes
Why Visit? This hidden gem is for adventure seekers and nature lovers. Home to Smith Rock State Park, it’s a paradise for rock climbing, hiking, and soaking in jaw-dropping desert canyon views.
Plus, Terrebonne has a laid-back vibe making it a perfect spot to unwind after a day of exploring.
Activities:
7. Ashland
Distance from Portland: 4 hours + 35 minutes
Why Visit? Ashland is a relaxing town that is known for its arts, culture, and outdoor beauty.
Activities:
- Rafting & Kayaking on The Rogue River (family friendly!)
- Ashland Escape Games
- Walk through Lithia Park
- Attend the Oregon Shakespeare Festival
8. The Willamette Valley
Distance from Portland: 1 hour
Why Visit? The Willamette Valley in Oregon is a beautiful, peaceful getaway known for its lush vineyards and rolling hills. This area is a perfect place for a girls’ trip, couples retreat, or any type of other trip.
Activities:
- Winery Tours from Portland (includes lunch!)
- Hiking
- Eat at one of the amazing local restaurants
9. Sisters
Distance from Portland: 2 hours + 50 minutes
Why Visit? This is a great spot for hitting the trails, biking around, or shredding some snow in the winter, it’s got plenty of outdoor action. The downtown area is super chill too, with cool local shops and great places to grab a bite after a day of exploring.
Activities:
- Endless hiking
- Eurosports (bike/ski rentals)
- Dan Anthon’s Just Add Water Fly Fishing (fly fishing charter)
- Horseback Riding
10. The Three Capes (Tillamook, Cape Kiwanda, and Cape Lookout)
Distance from Portland: 1 hour + 20 minutes
Why Visit? Visiting the Oregon Coast has a moody vibe experience. Tillamook is known for it’s cheese and ice cream (trust me you don’t want to miss out on tasting it). The towns are fun to visit with a lot of local shops, hot coffee, and endless oceanic views.
Activities:
- Tillamook Creamery
- Tillamook Air Museum
- Shore Thing Beach Rentals (kayak/paddleboard rentals)
- Haystack Fishing
- Grab a drink at Pelican Brewing Company
11. Crater Lake
Distance from Portland: 8 hours + 35 minutes
Why Visit? Crater Lake is straight-up magical. With its deep blue water and epic views, it’s the kind of place that makes you stop and just take it all in. Whether you’re hiking, driving the rim, or just soaking up the scenery, it’s a must-see.
Fun Fact: Crater Lake is the deepest lake in the entire United States AND one of the deepest lakes in the entire world?
Activities:
- Watchman Peak
- Rogue River Gold Nugget MidDay (whitewater rafting)
- Crater Lake Hospitality (boat tours)
12. Seattle, WA
Distance from Portland: 2 hours + 50 minutes
Why Visit? If you love sports, Seattle is known for being a big sports city. We have football, hockey, soccer, and more. For coffee lovers, a lot of visitors want to visit the original Starbucks. However, from a local’s perspective, there are SO many local coffee shops that are worth visiting.
Lastly, Seattle (and the greater area) has unlimited outdoorsy activities. Skiing, hiking, backpacking, paragliding, skydiving, it’s heaven.
Activities:
- Eat fresh sushi in Seattle
- Visit the Museum of Pop Culture
- Hiking
- Ski at Crystal Mountain
- Go to a Kraken game
13. Mount Rainier, WA
Distance from Portland: 3 hours
Why Visit? Standing as the highest volcanic peak in the contiguous United States is Mount Rainier.
During the summer months, the National Park Service requires permits and reservations due to the increase in visitors. See more here.
Activities:
- Hiking
- Camp Muir – pictured below – (not recommended for inexperienced climbers)
- Skyline Trail
Tips for Weekend Trips from Portland
⭐ If you’re visiting the city or exploring the trails, I recommend packing a waterproof & windproof rain jacket and waterproof hiking boots. For those who plan on busy and long days, bring a small daypack to carry essentials.
⭐ Don’t be afraid to ask a local barista or tour guide what their favorite thing to do is in the area. You will be surprised at what else you can visit in the area.
Weekend Trips from Portland Concluded
These 13 destinations are perfect for a weekend trip from Portland, whether you’re traveling solo, with your partner, friends, or family—there’s something for everyone.
From exploring the stunning Oregon Coast to sipping wine in the Willamette Valley or chasing adventures around Mount Hood, there’s no shortage of amazing getaways close to Portland.
Get ready to plan your next adventure!
Happy Trails,
Mindful PNW Travels
