5 Quirky Date Night Destinations in Portland

Date night doesn’t have to be the same each time. While we all love cuddling up at the movies or trying new restaurants or embracing a bit of high culture at museums, every once in a while, date night needs to be shaken up. Each city has a hidden world of strange, quirky, and delightful things to do. Try any one of these on your next date night and embrace the weird, whimsical part of life.

Bingo & Bourbon

Mississippi Pizza is a beloved Portland eatery with a lounge that puts on musical performances and hosts trivia nights. You can order classic, vegan, or gluten-free pizza pies, but whatever you order will be delicious. And, on Monday nights, Brian and Mike, host bingo. But this is not your grandmother’s retirement community bingo. No, this bingo is prank-filled, riotous, and never the same.  You and your date will love spending a night out here, because, whether you’ve played bingo before or not, the Bingo & Bourbon Nights at Mississippi Pizza are a wild, new adventure for date night.

Wyrd Leatherworks and Meadery

There is no other shop like Wyrd Leatherworks and Meadery. It is both a Leatherworks Shop (featuring gorgeous local, handmade leather goods) and a Mead Hall. Inside the Mead Hall, you’ll feel as though you’ve stepped back into Medieval Times or perhaps into a Viking Great Hall. It is a nerdy, unique, and utterly charming shop. Buy each other a locally crafted piece of art, then sit down to a large tankard of mead.

Shanghai Tunnels Tour

If you and your date enjoy history but are looking for a guided tour outside the norm, then the Shanghai Tunnels Tour is a must-do. Climb down to a hidden world that tells the story of Portland’s seedy past when locals were “shanghaied” (or kidnapped) and forced onto ships that were lacking in crew members. You’ll see unique architecture, underground holding cells, trapdoors, and more. There is no underground tour quite like this one.

Freakybuttrue Peculiarium

It’s all in the name. Nowhere will you find a stranger, quirkier date night destination. Freakybuttrue Peculiarium is a local artwork shop and museum featuring creepy & unusual exhibits. Get your photo taken in a photo stand-in and look as though you’re being dissected by strange alien visitors or wander through miniature crime scenes made from doll house pieces. Odd is the name of the game at Freakybuttrue, which is why you and your date are sure to love it.

Rose City Roller Derby

Are you and your date tired of cheering at traditional sporting events? If so, then it’s time to check out the Rose City Rollers, where you can watch the incredible game of Roller Derby, a contact sport on roller skates that will be sure to get your adrenaline pumping. Tickets for RCR Bouts can be difficult to come by, so be sure to reserve ahead of time.

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