20 Secret Places In Portland To Bring Your Girlfriend This Winter

Secret things to do in Portland this winter.
20 Secret Places In Portland To Bring Your Girlfriend This Winter

Winter in the PNW can make you want to stay inside and snuggle up with a marathon of corny Christmas movies. While your girlfriend probably enjoys that as much as you do, it's also important to get out and explore the weird city you live in and find new adventures to enjoy together—beyond just watching Elf for the 5th time this season.

Everyone loves a good surprise, and Portland has a few up its sleeve.  You can enjoy an absinthe tasting at a prohibition-style bar or learn about paranormal hauntings at PDX's own little shop of horrors

Whether you want to find a new watering hole for cocktails, discover a new park to stroll through with your babe and enjoy the outdoors or play minigolf under a blacklight, we've got some ideas for you! 

McMenamins Kennedy School

Where: 5736 NE 33rd Ave

We can say with certainty that this place got the memo on keeping Portland weird. This unique hotel was once an elementary school, and if you and your babe want something out of the ordinary, this is the perfect spot to explore. The "school" has its own brewery, a cigar lounge, an enormous soaking pool, and bars and restaurants to keep you entertained.

Even the guest rooms are decorated as classrooms. If you crazy kids have any teacher fantasies, you'll have plenty of props around to stoke your imagination!

The hidden bar at Circa 33 

Where: 3348 SE Belmont St

This throwback cocktail bar follows its prohibition theme to the T--including a secret back bar behind a bookshelf! Sneak to the back with your girlfriend to discover the charm of this swanky down-low hotspot.  

Blue Lake Regional Park

Where: 20500 NW Marine Drive

Via Oregon Metro

While this is an ideal spot to cool off in the summer, it's also a perfect place for a cozy, romantic walk during the winter. Bring your favorite coffee (or, whatever you want to smuggle in your cups!) and walk along one of the many paths that weave through the lush greenery and around the lake. If you're feeling adventurous, you can bring your bikes to enjoy the trails on wheels!

The Skidmore Bluffs

Where: 2206 N Skidmore Ct

This is one of the most romantic places to watch the sunset in Portland. While it's popular among the people who know about it, if you haven't yet discovered this gorgeous gem, then you'll definitely want to check this out! You'll get maaaajor brownie points if she hasn't heard of it!

On winter days that aren't absolutely freezing, you can bring a picnic and sit down to relax and enjoy great views, great company, and a stellar sunset over the city. To win even more bonus points with your lady, pack your picnic with the makings of a fabulous cheese plate. It's amazing how far a little brie, crackers, and grapes can take you!

The Goonies house

Where: 368 38th St

If your girl is a movie nerd, you'll score big by bringing her to the house from this famous cult film! Snap a few pics outside and make it a day to remember. This house is part of not just film history, but also Portland's classically weird role in it.  It's free and easy to drop by for a quick visit!

The Peculiarium

Where: 2234 NW Thurman St

If McMenamins Kennedy School got the note about keeping Portland weird, then The Peculiarium is the one who gave it to them. This one-of-a-kind establishment combines the playfulness of a costume shop with the thrills of a haunted house and the mystery of oddities in history.

It's a celebration of the abnormal, the paranormal, and the generally bizarre. Inside, you'll find a gnarly human-sized monster you can pose with, books you won't find in any Barnes and Noble, and even sometimes live actors in costume waiting to terrify you with a spooky performance. Bring your girlfriend here to get freaky together!

Glowing Greens Blacklight Minigolf 

Where: 509 SW Taylor St

If you like freaky, you might want to bring her to this blacklight miniature golf course as well. This funny game turns funky with dim AF lighting and neon highlights everywhere you look. 

 Shanghai Tunnels  

Where: 120 NW 3rd Ave

Explore the startling, strange history of the many men who were kidnapped and forced to work on ships that would be gone for years at a time. Walk through Portland's Underground and see the cells where men were held between their kidnapping and their departure on a ship.

The Garden at Elk Rock 

Where: 11800 SW Military Ln

The massive 13-acre state at Elk Rock overlooks the Willamette River as well as sprawling landscape and gardens all around it. The scenery evokes an old world charm, and its melding with nature brings a sweet serenity to the grounds. 

Take a romantic walk with your love and enjoy the beauty of all the flora and fauna surrounding you. 

Stark's Vacuum Museum

Where: 107 NE Grand Ave

If you're looking to change things up, this ought to do the trick! At long last, you can get answers to the burning questions you've always had about the evolution of the modern vacuum!

Rimsky-Korsakoffee House

Where: 707 SE 12th Ave

This cash-only coffee cafe is a colorful spot to go for an exotic dessert, a delicious fresh brew, and even live music that plays on occasion. 

If your lady is an Instagrammer, she'll have plenty of opportunities to snap some unique bathroom selfies and capture the unusual decor. 

 Chameleon Restaurant and Bar

Where: 5311, 2000 NE 40th Ave

This restaurant is just as visually enticingas its food is delicious. Chameleon serves a hybrid of Thai and American food, including such menu items as Green Papaya Salad and Hand-Made Tortellini.

True to its namesake, Chameleon is a shapeshifter with wide appeal. Their cozy backyard patio is used for a variety of events, including old movie screenings, enjoyed under a canopy of white string lights.  

The Box Social Drinking Parlour

Where: 3971 North Williams Ave

The Box Social Drinking Parlour is a colorful and stylish date option in Portland. Come in for swanky cocktails and choose a few snacks from their vegetarian-friendly food menu.

Check out their late-night happy hour every Thursday through Sunday 10 p.m. to close. See their full menu here.

Ash Bar at Nomad PDX

Where: 575 NE 24th Ave, Portland

The Ash Bar is a bit like an upscale speakeasy, hidden deep inside one of Portland's fanciest restaurants. This smaller venue is intimate and approachable with a rounded, conversational bartop. 

Guests can choose from the creative craft cocktail menu or taste from the eco-friendly food selection. 

The Secret Society Lounge

Where: 116 NE Russell St, Portland

Portland seems to be big on the whole prohibition-theme, and we're totally into it! The Secret Society Lounge is a small, sexy space that holds just under 50 people. 

They're known for their wide selection of absinthe, and they offer a tradition serving, complete with a sugar cube drip. 

Bagby Hot Springs

Where: Clackamas County 

Treat your baby to some Bagby! Okay, this one isn't technically in Portland, but we're including it as an honorary mention since it's worth the short drive if you want to escape to a secret spot just outside the city!  This sexy hot spring makes for a perfect daycation. Bring your sweetheart here to escape normal life and let it float away as you both sink into a sultry, steamy relaxation. 

The backroom at Langbaan

Where: 6 SE 28th Ave, Portland

For special occasions or nights when you just want to turn up the dial on dining, Langbaan is one of Portland's best. This Thai restaurant not only offers spins on traditional cuisine, but it also gives guests the rustic yet ambiance that lends to intimate conversation and memorable evenings. 


Where: 3525 NE M.L.K. Blvd, Portland and 2713 SE 21st Ave, Portland

This Scandinavian spa is a perfect place to detox with your babe without having to trek outside of the city. While Bagby can be a dreamy escape, sometimes convenience makes it all the more relaxing. 

This communal spa is unique in that it can be enjoyed as a couple. Most spas in the city are separated by gender, but this spa allows couples to enjoy the same area wearing swimsuits. 

B Movie Bingo at the Hollywood Theatre

Where: 4122 NE Sandy Blvd, Portland

There's nothing more fun than laughing with the person you love. If you and your girlfriend are fans of B movies, this is a night you'll want to put on your calendar. Test your trivia skills while you recall some of your favorite old movies--and maybe even learn about some you might have missed.

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