Cold weather in Portland often tempts locals to stay indoors and wait for the sunshine, but in our opinion, winter is the most romantic season of the year — and also one of the best seasons to explore the city. The chillier weather allows for plenty of opportunities to cuddle in a cozy bar with your sweetheart, sip a winter-themed brew, or catch the latest flick in a living room-style movie theater.
Next time date night rolls around, experience some of our favorite winter activities! Whether you’re in the mood for a luxe evening or some casual competition at an arcade, there’s sure to be an idea on this list to impress you and your sweetheart (and guarantee a second date).
Enjoy Some Oysters at Pepe le Moko
Winter is the best season to enjoy these delicious bivalves, and in the Pacific Northwest, we certainly know how to serve them up right! There are so many incredible oyster bars in the city, but one of our absolute favorites is Pepe le Moko. Located below Clyde Common and the Ace Hotel, the cozy, subterranean bar serves up a dozen freshly shucked oysters with champagne mignonette, horseradish and all the fixin’s.
Roast S’mores at Basecamp Brewery…
This popular, outdoorsman-themed brewery gives off so many cozy vibes, and with hollowed out logs for tasting trays, carabiners on the beer taps, and cozy fire pits on the patio, you might just feel like you’ve escaped into the woods on a weekend camping trip — only better, because you’ll have plenty of options for beer. Grab your brew of choice and head outside for a s’more-roasting session with your sweetheart. Good food and libations? Check. A romantic ambience? Check. We’ll leave the rest up to you.
….Or Embark on a Self-Guided Brewery Tour
Photo courtesy of Marcelo Moraes via Culmination Brewing
Portland is notoriously one of the best beer cities in America (maybe even THE best). Taste the flavors of our city and explore some new locales by sampling beers at some of our most popular breweries. Make a checklist beforehand and pick a few that are within easy reach of each other. You might end up getting caught in conversation and staying at the first spot all night, but that’s okay — it just means that your next date is already planned.
Catch a Movie at the Kennedy School Theater
Located in a converted school, this movie theater-meets-restaurant will take your cinematic experience to the next level. Order craft beverages, snacks and meals to be served to you while you enjoy the latest flick on plush armchairs, couches and the like.
Explore Your Artsy Side at the Portland Art Museum
Founded in 1892, The Portland Art Museum is the oldest art museum on the West Coast. Its mission is to engage locals and visitors alike with exciting exhibits of film, art and live interpretation. The artwork is curated from all over the world, so you are guaranteed to find something that inspires you (or spurs an interesting conversation with your date)!
Bonus: What’s better than perusing through beautiful art with your loved one? Viewing it for free! Stop by on the fourth Friday of each month for free admission, or $5 admission most nights after 5 pm.
Enjoy a Signature Cocktail at Portland’s Oldest Restaurant
Huber’s Café was founded in 1879, making it the oldest restaurant in Portland. And though its food and decor are modern, the eatery has not lost an ounce of its historic charm. The restaurant serves traditional turkey dinners, seafood and pasta, but the Spanish Coffee is truly the main event here. The bevvie is prepared table side with flame-filled theatrics, and the final result is full of flavor and just sweet enough — perfect for cold Portland evenings.
Take a Swing Lesson at Stumptown Dance
Bring your dancing shoes and get ready to tear up the dance floor at Norse Hall! On Sundays, you can enjoy a beginner’s swing dance lesson for just $10 per person, and then test out your newfound skills until 11 pm. This is the largest swing dance gathering in the area, and whether you’re a beginner or a seasoned pro, should be experienced at least once in your lifetime.
Explore Literature at Powell’s City of Books
Photo courtesy of Powell’s City of Books
Browse through the towering shelves at this local gem, which will likely be stocked with new and used titles ranging from politics to mystery. Chances are, the titles will spur an interesting conversation with your date, and some nights you’ll even be able to listen in to a live reading or discussion. We hear taste in literature is a good compatibility test.
Catch a Live Show at the Doug Fir Lounge
Portland’s music scene is truly off the charts. In fact, many of our country’s most popular acts are based right here in the Rose City! Doug Fir Lounge is the perfect place to catch these acts before they are discovered by the mainstream crowd. The venue is the perfect collision of old and new, and radiates that indie vibe that only Portland can pull off. It also offers a full-service restaurant and bar for pre-show provisions! During breaks, head to the patio upstairs and cuddle beside the fire pit. Sometimes (and especially on weeknights), you’ll be able to snag a ticket for as little as $10.
Hit up OMSI After Dark
This renowned children’s science museum might not be the first thing you think of for a romantic night out, but on the second and the last Wednesday of every month, the venue transforms into a 21+ club and throws a giant themed party with cocktails and appetizers. There’s no better way to bring out your inner child than exploring the exhibits with your sweetheart! Check out the events calendar to see which theme nights are coming up.
Try a New Restaurant
Photo courtesy of Alto Bajo Portland
The local dining scene is quickly evolving — so quickly, in fact, that it can be tough to keep track of our area’s newest and trendiest restaurants! Our city garners plenty of attention for its creative cuisine, modern atmospheres and quirky cocktail lounges. Impress your date and snag a reservation at one of these incredible Portland restaurants that opened in 2017. Who knows? You might end up returning in a year or so to celebrate an anniversary.
Compete At Ground Kontrol
Ground Kontrol is a bar and restaurant known for its large collection of new and antique arcade games. There’s nothing that guarantees a fun date quite like crushing the competition in a rousing game of D&D or Pac-Man, so grab a beer and the controllers, and let the games begin!
Pro tip: On the second Thursday and last Wednesday of every month, all games are free at Ground Kontrol with a $5 cover.
Love is in the Air!
Where is your favorite date-night destination in the Portland area? Let us know in the comments below.