Where to Go on a Perfect Date in Boston This Winter
From dumpling-making classes to cozy bars that are ideal for a first date.
It’s easy enough to hibernate for the winter. Conditions may be bracing, but there are still many ways you can socialize with your better half and brighten up some of the season’s darkest days. From top-notch bars for a first date to adventurous things to do with your longtime love, we’ve rounded up 28 stellar date ideas for the winter, whether you’re dipping a toe back in the matchmaking pool or simply looking to spice things up.
Various locations
There’s nothing more romantic than clinging to each other while slipping and sliding across frozen water. The rink at Frog Pond is the standard bearer, but if you seek a less kid-centric spot, The Rink at 401 Park caters to an adult crowd and is right outside both Time Out Market and Trillium Fenway, which means your food and drink options afterwards are far more epic than the usual hot chocolate stand. For more ideas, check out our list of the top destinations for ice skating across the city.
Take a beachside horseback ride
Ipswich, Massachusetts
Bet you didn’t even know that Crane Beach allows horseback riding in the offseason. North Road Farm offers guided, one- to two-hour beach rides all year round during low tide, allowing you and your sweetie to take your time and soak up those romantic vibes.
Drop in on an art class
Fenway
Whether you’re here to show off your creativity or have a good laugh over your shared lack of artistic talents, an art class offers plenty of opportunities for date night banter. The Saturday studio classes at the Isabella Stewart Gardner Museum don’t require reservations or even artistic talent, just the price of museum admission and a willingness to be creatively vulnerable in front of your new paramour.
Show off with a frosty sail
Boston Sailing Center
This is strictly for the sailing fanatics who have found each other, but yes, the Boston Sailing Center actually offers “frostbite racing” all year round on the weekends. Grab your first mate or assemble a crew and find a new way to explore your mutual love for the open seas (well, harbors).
Drink on a rooftop (yes, even in the winter)
Various locations
The Legal Rooftop Bar is the best of both worlds: high up and with water views, but made cozy by a retractable glass roof and a regal copper fireplace. If you’re feeling feisty, though, you can cuddle together under a blanket atop YOTEL’s ski-themed Apres...@ Deck 12 or inside the heated igloos on the Lookout Rooftop at The Envoy, Six\West Rooftop Bar, or the DoubleTree by Hilton Hotel Boston–Cambridge.
Sip wine beneath a bookstore
Beacon Hill
Beacon Hill Books & Cafe is the most exciting new bookstore opening in recent memory (oh, those fireplaces!). But it’s gotten even better thanks to its new subterranean cafe, which serves wine, beer, and savory snacks from 5 to 7 pm on Thursdays, Fridays, and Saturdays. If you’ve hooked up with a teetotaler, check out the Sunday afternoon tea service.
Various locations
Did you know that Blue Hills is just a few miles south of Boston proper and is even accessible by public transit? Not only that, but they even offer night skiing, when tickets after 5 pm are just $40 on weeknights and still grant you four hours on the slopes thanks to the ski area’s flood lights. If you’re hooked up with a more ambitious slopester, you can go a little farther afield to spots like Wachusett Mountain or Ski Butternut; simply check out our roundup of the best slopes and resorts to make the best choice for you and your boo.
Somerville
There are neither Oompah Loompahs nor edible rivers, but there is a whole lotta chocolate-making going on—and what’s sweeter than that? Taza was once a little-known hipster chocolatier delighting Somerville locals with its open-door policy. But today, it’s a national brand that still honors its roots and early fans. A tour will give you a primer on how to make stone ground chocolate, from grinding to molding (and, of course, eating).
Catch a concert at a new(er) venue
Various locations
Once upon a time, it felt like we were only losing music venues, not gaining them. But The Sinclair begat Roadrunner begat MGM Music Hall, and suddenly we’re awash in more show options than ever—all the better to determine if you’re musically compatible.
Get uber competitive
Various locations
If bowling doesn’t feel high-stakes enough, how does an ax sound? Ax-throwing, mini-golf, darts, ping-pong: our fair city is now fully immersed in the competitive games scene. Just don’t let your date win; no one should cater to a potential partner’s fragile ego.
Somerville
First, a primer: candlepin bowling was developed in Worcester in the 1880s and is a uniquely New England sport. The rules are the same as 10-pin, but the equipment is totally different with palm-sized bowling balls and narrow pins. Sacco’s Bowl-Haven is the perfect place for couples to try it out, with flatbread pizzas and beers delivered right to your lane.
Dorchester
The Museum of Bad Art is exactly what it says it is—but now, it has a new, more date-friendly home. Dorchester Brewing Company now hangs the fascinatingly horrible art throughout its first floor space; compare notes on your favorite piece of unsightliness while enjoying in-house brews and barbecue from M&M.
Enjoy a speakeasy steak
Downtown Crossing
Is there anything sexier than a delectable ribeye enjoyed behind a red velvet curtain? Bogie's Place, tucked inside jm Curley, is indeed a steakhouse speakeasy and one of the city’s coolest date-night options. It’s a chophouse just 18 seats strong, doling out classic cocktails, caviar service, a wedge salad, and surprisingly affordable steak cuts, adorned with the likes of bone marrow and foie-gras butter.
Cambridgeport
It was the date of your dreams when you were 14 years old—and you’ll love it just as much today. Grow closer with the help of A4cade’s nostalgic fun: classic ‘80s video games like Galaga and Ms. Pacman and a distinctly grownup cocktail menu. As for that food menu, what’s better on a first date than a couple of grilled cheese sandwiches with a soft-serve chaser?
North Andover
Okay, we’re heading into proposal territory with this one, but it’s pretty high on the romance scale: a private 45-minute tour over all of the city’s most iconic sites, including Fenway Park, the State House, and the USS Constitution. If the ocean beckons, you can instead choose the route that follows the Merrimack River and eventually floats above the North Shore and some of the state’s most beautiful beaches, which are somehow even prettier in the off-season.
Fenway-Kenmore
The architecture alone is enough to get you and your date excited—never mind the gorgeous courtyard that can give you a floral fix even on a cloudy day. While you’re there, swing by the glass-enclosed Cafe G for a romantic glass of wine and award-winning dessert.
South Boston
Who doesn’t love a good dumpling? Mei Mei has seized on that fact by offering dumpling-making classes inside its new South Boston location. Join a public class or splurge on a private afternoon of hand-folding and pan-searing.
Mission Hill
Looking for a nerdy date night? Tavern of Tales is Boston’s only board game bar, which means you can get off your couch without straying outside your comfort zone. Enjoy unlimited access to the massive board game library plus the opportunity to order from a full beer, wine, and cocktail list. A menu of comfort foods is also available including soup, sandwiches, and desserts like bread pudding and chocolate chip cookies.
Slurp one-buck shucks
Various locations
Are they aphrodisiacs? The jury is still out. But the placebo effect has to be worth something, especially when spots around town offer $1 bivalves, including Black Lamb, State Street Provisions, Viale, Lower Mills, Waypoint, Russell House Tavern, and more. Add a martini or two, and you have a date night you’d never know was budget-friendly.
Stargaze at Coit Observatory
Fenway
Luckily for lovebirds, the BU Coit Observatory opens up its facilities to all us non-scientific types every Wednesday night for its Public Open Night. The viewing starts after sundown and goes for about an hour, leaving you plenty of time for a romantic dinner afterward during these shorter days.
Climb some walls and celebrate with a brew
Somerville
It’s a lot more fun to work hard and play hard when you have a companion to join you for both. Start with a good old-fashioned forearm workout at Brooklyn Boulders. Once you’ve sufficiently impressed each other and/or humiliated yourselves, head next door to Aeronaut Brewing, where you’ll be asked to do nothing more than sit, drink, and be merry.
Embark on a walking tour of the city
Various locations
Download any number of the city’s self-guided tours, from the two-and-a-half hour Freedom Trail tour to the fascinating Black Heritage Trail or Women’s Heritage Trail, pop in your matching AirPods, and head out together. Or, harness your inner cartographer and wing it without any recorded guidance. Either way, it’s free, educational, outdoors, and great nerdy fun.
South End
On the first Friday of every month, the SoWa Arts District welcomes curious passersby into its hub of creativity. Artists fling open their studio doors, showcasing vibrant galleries and keeping them open late so you can explore cool works and artistic work spaces. Return on Sunday to shop at the dog-friendly SoWa Open Market and SoWa Vintage Market.
Sweat together (for less)
Various locations
PG-rated heavy breathing on the first date? It’s a good way to find out if you’re fitness compatible. Enter November Project, where early morning, large-scale group workouts take place atop the Harvard Stadium stairs among other outdoor locales, rain or shine, warm temps or cold. Go forth and flex.
Stroll through Boston’s prettiest streets
Beacon Hill
Sometimes simply ambling around one of our favorite Boston neighborhoods is all it takes to win over that special someone. Explore Beacon Hill (at night for extra ambiance) and take in the stunning brownstones for an easy-going but surprisingly charming time. Given all the little shops and restaurants stashed along Charles Street, you’ll find a new conversation starter around every bend.
Union Square
A quaint courtyard in the heart of Union Square, Bow Market has just about everything you need for a fulfilling first date, including outdoor dining, a brewery, and top-quality window shopping. And even though the nights are now shorter, you’ll still enjoy regular live music and other special events.
Coolidge Corner & Brattle Theatre
The iconic Coolidge Corner Theater offers first runs and midnight screenings, which you can enjoy while cozied up and noshing the best popcorn in town. If you’re a Red Line couple, the Brattle Theatre offers the same throwback allure.