5 Quirky Date Night Destinations in Boston

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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.


If you love travelling, art, and pure wonder then the Mapparium is a must-see place. It is a one-of-a-kind adventure that can be found in the Mary Baker Eddy Library. The Mapparium – a three-story tall, inside-out stained-glass globe of the Earth – is the only globe/map that offers an accurate depiction of the size of each country and continent on Earth. It is both a phenomenally breathtaking piece of artwork and an adventure which will have you questioning your own understanding of the size of the world.

The Boston Bricks

Are you and your date a couple of history nerds? Enjoy a bit of a scavenger hunt? Then it’s time to hunt for the history of Boston, Massachusetts. Take a lovely detour along Winthrop Lane to find all 100 “Boston Bricks”. The bricks are actually bronze reliefs, depicting important events in Boston’s history. They are placed among the bricks that line the pathway of Winthrop Lane. You may step on a brick depicting a sewing machine, the first baseball glove worn, or even a notoriously-aggressive Boston driver. But no matter where you walk, you’ll pause to laugh or ponder the quirky, important history of the city.

Museum of Bad Art

A title which is entirely subjective, but one which makes for a special trip to the museum. You and your date may be bored of attempting to add a little culture to your life. If that’s the case, then it’s time for a trip to the Museum of Bad Art. Whether the art is made by beginners or “professionals”, each piece has been considered “bad art” by traditional conventions of artistic worth. You may find inspiration to pick-up your paint brush again or simply enjoy wandering through art full of joy and no pretension.

Black Light Yoga 

Workout dates may already be on your list for date nights, but whether you consider them a classic date night option or something outside your current wheelhouse, you’ve never experienced a workout date quite like Black Light Yoga. The atmosphere in the studio is energizing, sexy, and fun. The black light will make you and your partner glow bright and neon as if you may have traveled to a sci-fi world. Flow through the poses in the glow of the black light while moving in time to the music. 

The Donkey Show

You may think a date night that includes seeing a Shakespeare play is a bit stuffy, but The Donkey Show has the cure for that. It is peculiar and fun, a show that combines Shakespeare’s bonkers comedy, A Midsummer Night’s Dream, with the bright lights and funky beats of the disco-era. Grab your feather boa and boogie to all the Disco hits of the 70’s while the magic of Shakespeare’s show unfurls around you.

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