Portland can be described in many ways. It’s progressive, rainy, and has one heck of a food scene. It’s also eco-conscious, artsy, and a beer lover’s paradise. I’ve been to the city once before during the summer and like many, I couldn’t wait to return. This time I headed to Portland during winter and if you’re wondering why keep reading. And if you’re heading there during that time, you’ll want to know all the fun things to do in Portland during the winter so keep reading as well.
So what brought me to Portland during the winter? A cheap flight for one, to visit a good friend, and because visiting places during the “off months” is less crowded and tends to be less expensive! Aside from that, winter is actually a great time to visit Portland because the city itself doesn’t get as cold at the rest of Oregon. Snow is rare in Portland but it did snow the week before I got there so it does happen from time to time. If you’re visiting Portland during winter there is plenty to do…
This post is in collaboration with Travel Portland who I was so excited to work with! Travel Portland kindly offered me the below food tour with Forktown along with complimentary admission to the Portland Art Museum and Lan Su Chinese Garden (which I loved so much from the first time I visited Portland that I decided to go again). All opinions expressed in this post are based on my personal view.
1. Go On A Food Tour
The city is FILLED with great food options and there are many tour operators that curate AMAZING tours! I had the pleasure of going on a tour with Forktown, a local operator that leads amazing food tours in Portland and around the world. I did the Downtown Portland tour which took me to delicious eateries where we sampled food, drinks, beer, wine, and dessert.
Owner of Forktown, Heidi lead my tour and gave us insightful information on each eatery. I felt like a VIP because we always had a seat and our food was ready to go. Check out some of the yummy things we indulged in.
Of course, you can go on a self-guided tour which I did the remainder of my days in Portland but the guided tour was such a great experience, I highly recommend it. Checking out the food carts is always fun and depending on food pod you go to there are heaters and canopies. If you love trying different foods I’d recommend going to restaurants during their “happy hours” so you can sample smaller portions.
Need Vegan/Vegetarian Options?
I can’t mention food without telling you about the Portland vegan options. If you’re vegetarian or vegan, you’re in luck because so many places have vegan, vegetarian, and even gluten-free selections. There are also various vegan restaurants such as Epif which is a pisco bar that serves up South American-inspired cuisine. Bye and Bye in the Alberta Arts District offers Southern-inspired vegan dishes and Virtuous Pie on Division Street has vegan pizza, vegan ice-cream and a whole lot more.
2. Go to a Museum
It didn’t rain a lot while I was in Portland but one of my favorite rainy day activities is exploring the city’s museums. I’m a sucker for art, and after taking three years of art history it’s become one the things I enjoy seeking out when visiting a city.
I got to visit the Portland Art Museum which has five floors of art. Explore ancient Asian art to American contemporary and so much more! I would recommend spending at least two hours here since it’s such a large museum. And if you’re looking for a deal on admission the museum offers free admission on the first Thursday of every month from 5–8 p.m. And every Friday admission is $5 after 5 p.m and grab wine, beer, and food at Art Pub at the Cafe.
Want to visit more museums? There are plenty!
Architectural Heritage Center
Oregon Historical Society
Oregon Jewish Museum and Center for Holocaust Education (OJMCHE)
Oregon Maritime Museum
Oregon Museum of Science and Industry (OMSI)
Portland Children’s Museum
World Forestry Center Discovery Museum
3. Go on a Bar Crawl
Did you know that Portland has the most breweries of any city in the world? And if beer isn’t your thing there are tons of bars serving up cocktails and wine as well. There is no shortage of bars in the city and here are some of my favorites:
Neighborhood: Northwest Portland/Nob Hill
Happy Hour: 4-7pm, and all day Monday
I must say I love a happy hour that goes beyond 6 p.m. It means more locals are likely to be present and since I was visiting my friend, she was able to join me after work. Pope House is most known for its bourbon but they serve up craft cocktail from all spirits. I didn’t get the chance to try one of their whiskey flights but they have an amazing selection. Oh, and the building is a house!
Neighborhood: Downtown Portland
Named after Abigail Scott Duniway, a leader in the suffragette movement and the first registered woman voter in Multnomah County. The space was once the Ladies Reception Hall which is where the suffragettes held their meetings. The interior has a modern meets early 1900’s vibe with fun cocktails and vintage glassware to match.
Neighborhood: Central Eastside
Happy Hour: 2pm-5pm Monday-Friday cocktails starting at $6 and food specials
Hey Love is a bustling bar and restaurant with rad decor that will have you feeling like you’re at the most amazing island beach party. The decor is amazing and I particularly enjoyed the food and enjoyed my boozy Pineapple Dole Whip.
Ash Bar at Nomad PDX
Happy Hour: 5-6pm $10 cocktails, $7 food all day
Ash Bar is small and intimate. It feels exclusive without feeling pretentious. The cocktails are quality, so if you’re looking to have a pleasant conversation with a friend or just want to enjoy some solo time, Ash Bar is the place to go.
Bible Club PDX
A prohibition inspired speakeasy inconspicuously located in what appears to be a normal house. Craft cocktails, a unique setting, and decor that will have you feeling like you’re in the 1920s.
The place to go if you want to eat, drink, and repent! Ready to confess? Head to the confessional, I mean the photobooth to take silly pics with your crew. Check out their Instagram for info on specials and events!
Neighborhood: Central Eastside
Happy Hour: Tuesday-Friday 3-6pm, and all day Monday
Soccer fan? Toffee Club is open early and closes late so you can watch all MLS soccer as well as teams from around the world! If you watch La Liga, Premier League, or any other international soccer or footy Toffee Club is a great place to watch. And they have great food and vegan options as well.
4. Visit Powell’s City of Books
The largest independent book store is located in the heart of Portland. While the streets of downtown weren’t as busy for Saturday, the bookstore was packed with book worms. I guess when it’s cold outside it’s the best time to find yourself a new book!
The store not only has a wide selection of books, it also carries merchandise like Harry Potter goods and Portland-inspired souvenirs. There’s also a coffee where you can start reading your new purchase!
5. Visit the Lan Su Chinese Garden and Explore Chinatown
If the weather allows, a visit to the Lan Su Chinese Garden is a must. It’s located in Chinatown and will have you feeling like you’ve been transported outside the city. There was light rain while I was there but it was so peaceful watching the raindrops hit the pond. We were lucky enough to catch a Chinese New Year-inspired performance. The Lunar New Year had just passed but the facility was still decorated with red lanterns.
After a visit to the garden, wander the streets of Chinatown. The gate is one of my favorite parts of Chinatown. And I love checking out the cool building signs.
6. Explore the Street Art
There are various murals throughout the city and some fun sculptures. The Zoobomb Pile is an ever-changing monument and piece of art, located just outside the Vans store in Downtown Portland. Walk the street and get mesmerized by the art. And don’t forget to visit the “Keep Portland Weird” wall.
7. Go on A Coffee and Donuts Crawl
Is that even a thing? Winter in Portland isn’t bad when you have coffee and donut to warm up to! If you need to get some work done and looking for a coffee shop or a cool donut shop to hang out you’re just in luck! Portland has various donut shops from the original Voodoo Doughnut location to the uber-hip Blue Star Donuts.
Voodoo Doughnut is fun and tasty but I wouldn’t stick around for coffee. There’s always a line, so prepare for that if you want to grab a donut or an assortment box. If you’re looking for a delicious sweet treat then head to Blue Star. They have various locations in Portland and offer great coffee and local tea by Steven Smith Teamaker.
8. Go Shopping!
Oregon has no sales tax so depending on where you’re traveling from you can be saving up to about 12%! It makes for a great excuse to shop. So if records, shoes, or vintage is your jam, get your shop on while you’re in Portland!
9. Go on a Road Trip
Portland is so close to so many things like the famous Columbia River Gorge, Mount Hood, and the Wine Country of Willamette Valley. You’re also less than 2 hours away from the coast and a few hours away from the southern part of Oregon. While you will have to check the weather before hitting the road some of these parts are even more beautiful during the winter.
Last trip I went to the Columbia River Gorge and Mount Hood areas and you can read about that here, but this trip I went down to Umpqua National Forest and drove the southern half of the coast. Umpqua was breathtaking with the snow and I had a great time soaking in the hot springs. And by surprise, it was sunny and not very cold during the day on the coast.
We headed all the way down to Samuel H Boardman State Park and drove up to Newport which is about halfway down the coast. The drive along the coast is long and deserves a few days because it’s absolutely stunning. I enjoyed Samuel H Boardman State Park and Bandon Beach.
Hope you enjoyed this post and found some fun things to do in Portland. Please Pin it for later!