I’ve lived in the Pacific Northwest for 11 years now and I’d say I’ve found my spot. I grew up in the South and am proud of my roots in Arkansas, but gosh. I think I was always meant to be a West Coast gal…I just didn’t realize it until my third decade of life.
Portland, Oregon has surely seen its ups and downs in the past few years, but I couldn’t be more proud to call it home. The people here care a lot…about humanity, about creativity, about food… and Portlanders are so genuine in our love of what we love. And we LOVE our outdoors, friends.
3 Day (Or Weekend) Trips From Portland, Oregon That Will Make You Want To Live Here
I mean, who wouldn’t fall in love with the outdoors when the gorgeous craggy-cool Oregon coast is under two hours away, the stunning Columbia River Gorge can be reached in an hour, and the internationally renowned Willamette Valley wine country is a mere 45-minute drive? We are spoiled. Rotten. And we’d have it no other way.
Here are my three favorite day trips from Portland complete with eats and sites to see along the way.
1. The Columbia River Gorge
Well, I had to start with this first because…it’s probably one of my very favorite places on Earth. The Columbia River Gorge sits just northeast of Portland and is an 80-mile-long, 4,000 feet deep river canyon that divides Western Washington and Oregon.
Cotopaxi windbreaker | cooler | dog pack | Danner boots
Quick Trip: You can start just outside Portland by stopping at the Sandy River in Troutdale for lunch (see below) and then head out on the drive through my favorite part of the Gorge. Or do a morning hike and stop for lunch on your way back to the city. Both would be fab. Even if you just have a couple of hours to drive out to the Gorge and back from Portland it is TOTALLY worth it, rain or shine.
Full Day: If you do have a bit more of your day, I highly recommend a trip to Hood River, just one hour from Portland. You get a beautiful drive through the Gorge and then can visit one of the cutest towns around, have some lunch and do some local shopping. Grab a beer down by the river and check out the windsurfers — the town is known as a windsurfing destination. If it weren’t so windy we would live there already. I LOVE Hood River. Check out my list below for some places to stop there.
See More: While you could easily spend your whole day hiking and exploring Hood River, it’s worth it to hop over to the Washington side of the Gorge, for additional amazing views and delicious food stops. Some of my favorite wineries are in and around Lyle, Washington, just 15-20 minutes from Hood River — across an iconic bridge! Most require tasting reservations, FYI. If you want to stay in the area, The Society Hotel is lovely, but books up quickly! If you want to stay in Hood River, we love the Best Western (trust me) and The Hood River Hotel. There are also lots of Airbnbs in the area!
Things To See, Eat & Explore In The Colombia River Gorge
See: Sandy River in Troutdale (sneak peek in my Reel here), Multnomah Falls (super popular lately, needs a reservation), windsurfing in Hood River, COR Cellars (WA side), Syncline Winery (WA side), shopping in Hood River on Oak St (don’t miss Plenty Boutique).
Eat: Closer to Portland — Sugarpine Drive-In (do not skip this!), McMenamins Edgefield (a hotel and grounds with multiple options), Migration Brewing in Gresham. In Hood River — Double Mountain (best beer and pizza!), Pfreim Brewing, Solstice Pizza, Broder Ost (Scandi breakfast), Doppio Coffee, and the Gorge White House.
Explore: Beacon Rock (WA side), Punchbowl Falls, Horsetail Falls, Eagle Creek, Cathrine Creek (WA side), Klickitat Trail (WA side), Dog Mountain (WA side), The Fruit Loop, Lost Lake, Angel’s Rest.
2. The Oregon Coast
The Oregon coast is definitely famous and I probably don’t need to tell you a ton about it, BUT we’re so lucky it’s so close to Portland.
Quick Trip: We most often visit Cannon Beach as it’s the closest with the most to offer as far as shopping, restaurants AND iconic Haystack Rock, but there are many adorable places to see along the coast if you have more time.
For the purposes of this article though, and the focus on Day Trips, I’ll mostly stick to places near Cannon Beach.
Full Day: If you have a little more time though, exploring farther south outside of Tillamook and into the Capes is a really lovely area! Also, Astoria, Oregon is just a 40-minute drive north of Cannon Beach and a fun route to take on the way home back to Portland. You can stop for dinner there at Buoy Brewing or our fave, Fort George (get pizza and a Sunrise Oatmeal Pale Ale!)
Sweatshirt | Jeans | Bag | Sneakers
Things To See, Eat & Explore On The Oregon Coast
See: Haystack Rock, shopping along Hemlock St (much more than just tchotchke shops,) Arch Cape, kite flying on the beach (great kite shop in town if you forget yours!)
Eat: Ecola Seafood Restaurant (new awesome patio seating!), Sea Level Bakery + Coffee (get the PB cookie!), Driftwood Restaurant, Pelican Brewing, Gatsby’s, and Bill’s Tavern.
Explore: Ecola State Park, Astoria (site of many 80s films, the confluence of the Columbia River with the Pacific Ocean, Ft Stevens), drive Hwy 101 from Cannon Beach down to Tillamook…it’s gorgeous!
Fleece | Similar Backpack | Vest
3. Willamette Valley
Just 45 minutes south of Portland proper, Willamette Valley is becoming one of the most sought-out wine regions in the country. Gah, if you love a Pinot Noir you will be in heaven. And I love a Pinot Noir. The SEE here will be wineries because that’s what there is mostly to see here but gosh. There are some fabulous spots. My parents used to work in the wine industry years ago, so I have developed their palette. Our recommendations might be a little different from other lists but trust me on these…they’re all amazing!
Quick Trip: You really can’t go wrong if you just want to hit up a few wineries right on Archery Summit where De Ponte Cellars (see below) is located as well as quite a few others. You will have a lovely time.
Full Day: If you have more time to explore, I highly recommend doing a winery or two before lunch in Carlton, having lunch in Carlton or Dundee, and then perhaps one more tasting in Dundee Hills before heading back. You could stop for dinner in Lake Oswego at our friend’s restaurant Tavern on Kruse.
See More: McMinnville it’s so much fun for an overnight or two! I’ve detailed a few places below to eat and stay. The downtown is super walkable and even has outdoor dining nights in the summer and early fall where they block off some of the streets. It feels quite festive and European!
Things To See, Eat & Explore In Williamette Valley
See: De Ponte Cellars (Dundee), Sokol Blosser (Dundee), Keeler Estate Vineyard (Amity), Tendril Wine Cellars (Carlton).
Eat: Red Hills Market (Dundee), Dundee Bistro (Dundee), La Rambla (McMinnville), Thistle (McMinnville), Ōkta –very fancy, book way in advance (McMinnville).
Explore: The Allison Hotel spa, thrift shopping in McMinnville, Left By West boutique (McMinnville), Chapters Books + Coffee — tiny but awesome (Newberg), and stay at the Atticus Hotel (we loved it!).
There is so much to do and see right outside Portland, but hopefully, this list of my very favorite day trips will get ya started.
Want to keep up with everything else I’m into? Pop over to my Instagram @laurajansenstyle where I love talking about food, sharing OOTDs, posting travel pics and chatting everyday mom-life-stuff from Portland, Oregon. Oh, and lots of funny memes and pet videos because what is social media without plenty of those. xoxo
Ohhh, so timely. My partner and I are currently planning a trip up the coast – flying into San Francisco and driving to Seattle, with an emphasis on Oregon!! Thanks for the tips. Can’t wait to visit Sokol Blosser after doing so, many many years ago!!
Oh wonderful, Heather! I hope you enjoy!!
I’m from Portland and have hiked Angel’s Rest – I’m impressed Sienna did it!
Thank you! She did great! Wish I could bottle her energy haha. It’s such a worthwhile view at the top.
This is making me want to book a trip right this second. I did a road trip down the coast in 2019 that has only made me want to return over and over. And I love wine and wineries. And hikes. And rivers and mountains. I’m not really sure why I don’t already live in Portland sometimes, to be honest. I’ll definitely bookmark this post for the next time we make it out there!