Portland, Oregon has tons of things to do for visitors of all sorts. It’s known for being a hipster city, but it’s so much more. There is great food, lots of art, spas, parks and it’s the gateway to the Willamette Valley wine region. Portland can be a home base for a week long Oregon vacation or just a weekend getaway.
These are our top picks for planning a chill and fun weekend in Portland. If you have additional recommendations or questions, leave a comment or send us a note. We’re always happy to help!
Why Choose Portland for Weekend Trip?
Have you ever been in search of the city that you really feel like could be your second home but you don’t want to go where everybody else is and yet you want to be around all kinds of awesome people but you want small/local options but you want awesome food but… Well, that’s Portland. It’s set in an incredibly beautiful area right on the Willamette River in Oregon. Depending on where you are, you’ve got a gorgeous view of Mt Hood and you’re set up for day trips to a variety of interesting places.
Traditionally we skip over Portland because we’ve just not been familiar with what makes it worthwhile. We use the bypasses to avoid the city and head directly to the waterfall area of the Columbia River Gorge or just directly out to the coast, but not anymore.
This weekend getaway plan is perfect to experience the Portlandia you might expect if you’ve ever watched the show. With just two days in Portland you’re able to have incredible sushi and Asian cuisine, breakfast that’s free range somethin’ rather, a spa day that feels like Finland, more free range food, awesome craft cocktails, another free range breakfast and so much more. So, some of that is exaggeration, but it does seem like everything in Portland is free-range, organic, gluten free, small batch, craft ________ (add your favorite product here, basically). It’s a good thing.
And then the wine. If you’re not planning one, you need to go back for a wine weekend, because here’s a quick note about what to expect: they’re crazy for their Pinots and they are passionate and knowledgeable about the whole wine industry in Portland and all through the Willamette Valley. Having worked with lots of wine folks over the years, I appreciated their fervor.
How to Get to Portland, Oregon
We always drive to Portland, but that’s not what we’re going to recommend unless you are already in Oregon or Western Washington. Here’s the scoop: if you’re coming from any city that’s not Seattle, you’ll want to fly into PDX. Depending on your ultimate plans for your Portland weekend getaway, you don’t need to have a car in the city. You can take the light rail from the PDX airport into the city. Once you’re there, everything is a short walk or an Uber ride away.
Tip: you can rent a car for a day or two so that you can go experience the Columbia Gorge waterfall area which includes Multnomah Falls, or go tour Willamette Valley wine country for load of Pinot Noir… or head to the coast to experience some lighthouses and jagged coastlines… but these options are for a bit more than a Portland weekend getaway.
Getting to Portland from Seattle
If you’re coming from Seattle, you could take the train from downtown to downtown and you’ll have a beautiful, relaxing ride, but the Amtrak ticket it quite pricey. If you can catch Amtrak giving some good deals, snatch those tickets up right away!
Note: when we looked for train tickets to Portland this fall, prices were around $170 per person for round trip.
The best way to get to Portland, for a long or short weekend trip, is via the FlixBus. It’s a very nice motor-coach that’s comfortable with wifi and no worries. The FlixBus is really ideals to get to Portland from Seattle. Between the cost of gas and two nights of parking, you’ll be spending $150 at least, so you might as well spend the less than $50 round trip per person to be able to have a great ride to Portland from Seattle and save some cash.
Things to Do in Portland
Being a major metropolitan city, there are plenty of things to do on a weekend getaway to Portland. Whether you’re visiting Portland with kids or if it’s an adults only trip will have an impact on what you choose to do. If you’re spending a few days here as part of a Washington / Oregon road trip, make sure you take time to enjoy the neighborhood side of the city, not just the tourist sites.
Things to do With Kids in Portland
I’ll be the first to tell you that any city trip with kids is going to be very different form an adults only trip. Portland with kids is really fun though, as Washington Park and Macleay Park are both great to explore. You’ll love the Oregon Zoo and Forestry Discovery Center in Washington Park. Then nearby Macleay Park actually has some wonderful hiking trails… and it’s surrounded by neighborhoods!
Visiting the OMSI, Oregon Museum of Science and Industry, on the river is a fun idea, especially if it’s a rainy weekend in Portland. Neary the OMSI is the Portland Art Museum, which brings in amazing exhibitions of famous and modern artists. And then in summer months, there are always things happening in the Pearl District that kids will love, including farmers markets.
Gardens to Visit in Portland
Portland, Oregon is known as the City of Roses, but there are way more gardens to visit in Portland than just the famous International Rose Test Garden. You’ve got the Rose Garden, the Crystal Springs Rhododendron Garden, the Hoyt Arboretum, the Portland Japanese Garden, the Lan Shu Chinese Garden, the Dunaway Park Lilac Garden and more. Spring and summer in Portland smell really nice.
Family Friendly Willamette Valley Wineries
Within a little over a half hour of the city, the Willamette Valley opens up and you’re surrounded by wine country. If you want to go wine tasting with your adult buddies or if you’re looking for family friendly Willamette Valley wineries, you’ll have plenty of choices.
Plan to go south to Newberg, or even as far south as Monmouth for wine tasting. Pinot Noir is going to be the highlight of the trip, but there’s a wine for everyone. And most wineries do have kid-friendly menus and activities.
Shopping in Portland
I’m not a shopper and we try to encourage our kids to be thoughtful about purchasing items (with their cute tiny handfuls of coins), but Portland is amazing for shopping. We went down with the intention of two things: getting a small amount of Christmas shopping done and finding a warm layer for under my jacket.
A huge bonus for those of us from Washington State is that Oregon doesn’t have sales tax. We love to do our shopping in Oregon as the bang for your buck is very visible. And it kind of feels like it’s the land o’ sales.
Tip: if you are indeed a shopper who likes to visit chains or larger department stores, then downtown Portland is great, as it’s got all of the fun high-end and mid-grade stores you may want to shop at, but also has an incredible selection of local, Oregon stores.
For my quest to get a warm coat-type piece to make me a little more comfortable in the frigid Portland wind, I was so excited to find a Mountain Hardwear store where I could get the most ideal Oregonian down vest. I know, sounds silly, but it’s the perfect thing you need to be warm but also trendy and hipster (which is Portland to a tee).
If you’re planning on seeking out local or unique handicrafts, there’s the Saturday Market (seasonal) or the Urban Air Market. Both of these events happen in/around the Pearl District and offer the most uniquely Portland shopping experiences possible. The Urban Air Market, when I stumbled across it, was being held in the basement of a parking garage. Portland. 🙂
Shopping in Portland’s Chinatown District
Unlike the International District in Seattle or San Francisco’s Chinatown, the Portland Chinatown area is very quiet. We always love to visit International Districts for wonderful food and unique shopping, but it isn’t as awesome in Portland as other west coast cities. Victoria BC has a wonderful Chinatown for exploring, shopping and food, and Los Angeles has several different IDs. Pop in if you’re feeling inspired, but don’t plan your whole day around it.
Note: if you love the Portland ID, please leave a comment with your recommendations for visiting. We’ve never been when it’s been busy or during any festival, so our experiences have been very quiet.
Plan a Portland Spa Day
Having a spa day during a Portland weekend getaway is a great idea. It’s okay to dedicate a few hours once or twice a year to clearing your mind and just relaxing, so adding it to a Portland trip is ideal!
After some intense research and trying to find a spa experience that would be good for men, I discovered Loyly Northeast. This place was awesome!
Note: this was my BFF’s first time doing a spa day and I wanted it to be a totally comfortable and awesome experience, so finding a place that was co-ed, had social and silent Finnish saunas and offered quality dude-treatments was the goal. And it rocked.
I booked us the Rejuvenator Deluxe and it was perfect. Per the Loyly website our package included “90-minute massage, aromatherapy foot soak, up to two hours in the sauna facility, single-use rejuvenating mask, sparkling water, cleansing tea and a single-use body salt.” We weren’t rushed through any of our treatments and had great staff attending to us. I was personally very happy with the LMP who worked on me, as she used several different massage techniques and genuinely listened to me as my 90 minute massage played out. Really, I was feeling so awesome at the end of it.
And then I got to do a sauna and foot-soak after… I wish this was an every weekend sort of thing. Chris and I are already plotting out our trip together down to Portland and we’ll for sure be spending an afternoon at Loyly Northeast. Maybe we’ll just move in.
Note: we did have a day at the Waterleaf Spa at Skamania Lodge on the Columbia River and it was awesome too, but Loyly was a completely different type of spa experience. A fun activity would be to do a weekend in the Gorge and do the spa and then also do a weekend in Portland and do a Loyly spa day. Totally different experiences.
Kayaking in Portland, Oregon
There is even kayaking in Portland, like, downtown Portland! There are quite a few boat launches on the Willamette River to be able to paddle along the Portland waterfront. If you don’t want to do the urban kayaking thing, head just to the south for wine country kayaking or head east to see what you’ll find in the Columbia River Gorge or the Cascades. Lots of options!
Check out our Guide to Kayaking in Portland, OR!
Where to Stay in Portland: Hotel Vintage
Portland has some really fun hotels and vacation rentals. If you don’t want to be directly downtown, say maybe closer to Oregon Wine Country or the route to the Oregon Coast highway, consider a short term private rental INSTEAD of a hotel…
For our weekend away, we got to stay at the Hotel Vintage, a Kimpton Hotel, right smack in downtown Portland. It was really cool, hip even. Being a wine themed hotel AND being in what’s apparently the coolest city I never knew was cool, the Hotel Vintage was dripping with subtle, local viticulture. Our room was comfortable and themed by Ebony Wines (an Oregon winery). It was wonderfully clean and quiet, and was the perfect home base for our weekend.
The Hotel Vintage (and other Kimpton hotels) offers a daily wine hour, but since we missed it due to traffic, they gave us a few vouchers to grab something from the lobby bar, Bacchus. The bartender was oozing Portland-cool and made a killer dirty martini.
We also took time hanging out in the lobby before leaving the city because THERE IS A POOL TABLE and SHUFFLEBOARD. I’m a sucker for table games and love getting to play them with the kids… but since it was Jon and I he had to play instead. Feeling at home, feeling welcome to have fun, and being centrally located were all key selling points for having the Hotel Vintage as our home for the weekend.
Tip: if you’re not already a member, you can join their Kimpton Karma rewards program for free wifi. Completing your profile is a great way to get some value as well as make sure that your future stays have delightful little surprises built into them.
**Disclaimer: I used to work for Kimpton Hotels and love everything about the brand and their service, so I was an easy sell with such a cool place.
Where to Eat in Portland
Okay, everybody has different tastes in food and atmosphere and we really got the gambit during our Portland weekend getaway. I’m only sharing four places you need to go, but the city is kind of a treasure trove of yum, so go explore!
Sushi. I don’t think I need to say much more. Well, let’s just say that the rolls were beautiful, the fish was tender and fresh, and the poke was on point. No Seattle or Portland weekend getaway is complete without sushi. Bamboo Sushi was great for several reasons, but the quality of the fish is at the top of the list. If you’re only ordering rolls that mask the fish and stuff, then go wherever and you’ll be fine. If you want sushi that’s subtle and showcases the fish AND has a really great atmosphere, Bamboo sushi is perfect. We sat at the bar and only had to wait a few minutes to get drinks and then the food started showing up.
Cheryl’s on 12th
While the cheesy hash-browns, scramble and croque monsieur were all delicious, the item that really stood out was the Bloody Mary. For realz. I’ve had my share of Bloody Marys and this was the best tasting one yet. I asked what the scoop was and one of Cheryl’s daughters told me: smoked paprika. She wouldn’t give any more details and wouldn’t share anything else from the recipe but teased me with just that. OMG. It was the best.
The staff was all really great too. The restaurant is called Cheryl’s on 12th… and we met Cheryl and her husband and two of her daughters and a bunch of other people. We had such a great time and loved the food so much that we went back on our second morning for one more dash of atmosphere (we knew it was Christmas sweater day) and to get some cookies from their cafe counter for the drive back to Seattle.
Note: Portland is ALL ABOUT BRUNCH. I thought SFO was big on brunch, but Portland takes the cake. It’s busy everywhere and you’ll have 100000 choices. Get to Cheryl’s early for a faster seating. And have a Bloody Mary or two.
Expatriate: top Portland Dinner Pick
If you know me in real life you know that I hate loud places, whether it’s a children’s museum or a bar, if it’s loud, I’m not a happy camper. Well, Expatriate is loud… but it’s because they’re blasting 1970’s vinyl!! I will happily sit through scratchy records for incredible Asian-fusion.
Fusion. That’s such an over-used word in West Coast cuisine. Expatriate does it properly though. We killed a fried Brussels sprouts something rather and then put away Laotian tacos served on leaves and finished with some sort of corn and crab ramen. Holy! Consider me fused.
Seriously though, Expatriate is located outside of the downtown area and is a great way to experience another part of the city. It was actually really close to Loyly (our spa day) and had some other really cool, dare I say hip, establishments directly next to it.
Tip: Expatriate is in a neighborhood, so know that you’re parking situation might be lame, so best to take an Uber or something.
I had another Bloody Mary here at Bijou and it was good, but not as good as the one at Cheryl’s. 🙂 And then I learned about harissa. So, harissa is this amazing North African/Middle Eastern paste/sauce that is so delicious and made with roasted peppers, cumin, mint and so much more. Now, take that and mix it with roasted potatoes, cauliflower and kale (because you’re in Portland and it’s kale), and you have the best breakfast dish I’ve eaten in who knows how long. Bijou Cafe wins for the best breakfast dish for now… until we come back to Portland.
We also got cornmeal pancakes with honey butter and fried chicken and that was amazing too. I’m pretty sure we could’ve gotten anything and would’ve been completely satisfied.
Tip: get there early and don’t think you can just go sit at the bar. Those seats are on the check-in list too and you have to wait (lesson learned).
So yeah, that’s how to spend a great weekend in Portland, Oregon. You can elaborate on this plan in so many ways. Add a coffee tour, some breweries, a day in wine country, and countless more restaurants to the list of PDXperiences. Spending a weekend in Portland completely will change your view of this awesome city you’ll want to return.
For more Oregon travel ideas, consider these great trips:
- Columbia Gorge Waterfalls
- Astoria and Seaside, Oregon
- Complete Oregon Coast Road Trip
- Visit Bend and Central Oregon
- Explore the Painted Hills of John Day Fossil Beds National Monument
- Cascades and Waterfall Oregon Road Trip
- Complete Oregon Bucket List Loop Road Trip
Wednesday 25th of January 2017
This is awesome! I've been wanting to check out Portland for a while and being from Vancouver the getting there and back is a bit tricky, esp. for the weekend. I'm really stoked to hear that brunch is a big deal here... it's a big deal for me too, but harder to find the full on organic ones that I LOVE so much :-)
Tuesday 20th of December 2016
Looks fantastic place! I have added this in my bucket list. I have just heard about it, but never been thought to visit. Thanks for inspiring me. Now I will definitely plan for it. Thanks again.
Wednesday 14th of December 2016
Portland also has some great craft/small chocolate shops. Creo has "make-a-bar tour" - you get a tour, then design and make your own bar.
Thursday 15th of December 2016
And I found a great small batch candy shop called Quinn. They do mic and match of interesting fruit gum drops and such...
Monday 12th of December 2016
Portland seems to have a really creative vibe! Love the thought that you put into your BFFs spa experience. Would love to try the pancakes at Bijou Cafe too!
Sunday 11th of December 2016
I adore Portlandia and would want to experience that Portland when I go! I can't believe we've never been to Portland, so this will come in handy when we finally make it that way. Thanks for a great guide!