Winter Date Ideas in Boston that Aren’t just Dinner & Drinks

When:
Wednesday, Feb 01, 2023 9:00a -
Saturday, Apr 01, 2023 10:00p

Where:
Boston
Surrounding areas
Boston, MA

EventScheduled OfflineEventAttendanceMode

Admission:
$Varies

Categories:
Art, Date Idea, Drinks, Food, Games, Movies, Music, Nightlife, Party, Seasonal, Shows

Event website:
thebostoncalendar.com

Temperatures are dropping, but there’s no reason to curl up all alone. In fact, winter’s one of the most romantic times of the year, and there are plenty of excuses to cozy up with the one you love. But instead of repeating the same old hot chocolate date, it’s time to spice it up this cuffing season. We’ve rounded up the most unique date ideas that’ll get you through to spring.


By Kenneal Patterson


Explore winter nature


Too much time curled up on the couch (blasting the space heater) might have you missing sunny days in Boston’s natural spaces. If you and your SO are the outdoorsy types, the single digit temps can be a real bummer. But fear not: you can live out your adventurous fantasies in winter, too. Explore Chestnut Hill under the romantic moonlit glow, get in touch with your inner self at a Fro-Zen Mountain Summit, or take a winter wander at Peddock’s Island in search of critters and tracks. If you’re looking for something closer to home, warm up with a run at Jamaica Pond, stretch it out with a weekly walk with Frost Fit.


Fine dine with someone fine


We get it, there’s nothing more classic than a dinner date. But with Valentine’s Day right around the corner, it can seem almost impossible to get a reservation at the perfect date night spot. Instead, why don’t you try some of our favorite walk-in spots? There are mouthwatering options, fit for everyone: tacos and margaritas at Lone Star, comfort food and karaoke at Highland Kitchen, cocktails and craft beer at Drink, and so much more.


Spend a cozy night at an apres-ski


You might not be skiing in the Alps this winter, but that doesn’t mean you can’t enjoy the Aprés-ski perks. There’s nothing like enjoying a hot toddy or mulled wine with good company. Whether you’re on the first date or with a long-time partner, enjoy the Apres-ski experience at Bow Market’s Ski Bar Popup for hot drinks galore, sample the butterscotch fondue at Aprés at Deck 12, and enter an alpine oasis at Publico Boston, where you can sit on plush couches and admire a vintage ski lift. If you’re looking for something quaint and private, book out a yurt at the Bowery. 


Treat your date to a creative experience 


First round’s on me, second round on you? There’s nothing more fun than sampling Boston’s most delicious and decadent cocktails at the coolest bars around the city. If you’re surprising your SO with something creative, look no further than Boston’s many experiential bars, and challenge your date to a game of pickleball at PKL, ping pong at SPIN, or mini golf at Puttshack! And every Sunday night at Silhouette Lounge, enjoy an exciting night of pinball (and a shot of winning the $50 grand prize!) For something fancier, there’s also Eataly’s Valentine’s Soiree (complete with vino and cheese!)


Find a romance novel 


Do you like to spend your evenings curled up with a copy of Pride and Prejudice? If you’re a bibliophile, it’s time to live out your perfect love story IRL. But no need to skip out on the books: take your date to the Boston Public Library and spend the day sipping a cuppa tea at the BPL Tea Room (and end the night at a Tea Infused Cocktail Lounge). Or, explore Boston’s independent bookstores: find a story at the new Beacon Hill Books & Cafe and grab a delicious cocktail at Tres Gatos Book and Record Shop. Check out a novel (for free, of course) at Boston’s famous libraries, and stop by 10 ½ Beacon Street for a guided tour of The Boston Athenaeum. 


Get away for the day 


If you and your SO are looking for a winter getaway, why not take a day trip and get some fresh air? Practice your snowshoeing skills at Weston Ski Area, hit the slopes at Wachusett Mountain, and feel the wind rush past you while tubing at Nashoba Valley Tubing Park. If you venture farther, you can live out your fairytale dreams at New Hampshire’s Ice Castles, a never-ending labyrinth of caverns, tunnels, and slides made entirely of ice.


Try out a creative class


There’s no reason to check off every New Year’s resolution alone. Two’s better than one when learning new things, and a new class is a great way to stimulate your creativity or your mind. You and your SO could take a photo workshop class by day or by night, try your hand at woodworking, fuel your artistic alter-ego at an MFA Studio Art Class, or do something a little more casual (while belting out top hits) at a Taylor-Swift-themed painting class. 


Stay active (despite the chill!)


When the January breeze blows in, it can be hard to even leave your house, let alone exercise. Your date is the perfect person to motivate you to stay active, and doing it together is twice the fun. You can get your blood pumping by learning to curl, snowshoeing, tubing, ice skating (pro tip: when the Public Garden is frozen, you can skate there for free), and even sledding (when the weather allows). Or, to make your heart race extra fast, share a glance with your good-looking date!


Let it heat up with dancing


It’s about to get caliente. Salsa dancing is a dance for lovers, so don’t be afraid to grab your date’s hand and spin them round. As the Latin music swells and you coordinate your fancy footwork, you’ll be falling for your date (literally!) Check out salsa dancing at The Dante Alighieri Cultural Center, swing dancing at Q Ballroom, or Dance to the Music of the World every other Friday night in Arlington. 


Don’t let the winter blues get to you. You and your special someone can stay warm during these cozy winter dates. 


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Photo by @kaylamaria13


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