Where to Go on a Date This Winter in Boston

It’s time to get cozy.

Variants be damned, in-person dating is still alive and well. But it can be tough to co-mingle in the middle of winter. Believe it or not, Boston can still surprise with its couple-friendly excursions, even when our walkways are icy and our daylight hours scarce. We’ve rounded up 19 stellar ideas for you and your date to enjoy all day or all night long this winter, whether you’re dipping a toe back in the matchmaking pool or simply looking to spice things up with your longtime love.

Canton
Did you know that Blue Hills, one of New England’s go-to ski mountains, is just a few miles south of Boston proper and is even accessible by public transit? Not only that, but lift tickets after 5 pm are just $35 ($40 on the weekends) and still grant you several hours on the slopes thanks to the ski area’s bright lights overhead. If you crash, though, it’ll be much less embarrassing under the cover of night, and ski lift rides are that much more romantic.

The Boston Common Frog Pond
The Boston Common Frog Pond

Or warm up with a little ice skating

Various locations
There’s nothing more romantic than clinging to each other while slipping and sliding across frozen water. The rink at Boston Common’s 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 Brewing, which means your food and drink options afterwards are far more epic than the usual hot chocolate stand.

Take a dumpling class with your dumpling

Online
One thing that came out of this pandemic: a collective deepened love of dumplings. Mei Mei has seized on that reality by offering virtual dumpling-making classes that have remained wildly popular. Settle in for a cozy evening of hand-folding and pan-searing.

Boston Sailing Center
Boston Sailing Center

Show off with a frosty sail

Boston Sailing Center
This is strictly for the sailing fanatics who have already found each other, but yes, the Boston Sailing Center actually offers “frostbite racing” all year round on the weekends. Find a crew and find a new way to explore your mutual love for the open seas (well, harbors).

Indulge in a staycation at a new(ly refreshed) hotel

Various locations
What better time to rediscover one of our city’s hotel stalwarts? To celebrate its 50th year, The Colonnade Hotel has undergone a massive renovation that embraces the space’s Brutalist exterior with beautiful mid-century decor. Plus, you don’t even have to leave the building to enjoy a romantic meal—Lucie will take care of you nicely with its global, French-leaning menu.

Publico Boston
Publico Boston

Skip straight to the apres ski

Publico Street Bistro
We love it when we can forgo exercise and head straight to the fun stuff. Publico Street Bistro is bringing back its chalet-inspired wintertime pop-up, The Lodge at Publico, full of flannel blankets and pillows, faux moose and deer heads, and even an artificial snow machine. Share a punch bowl with your sweetie while snuggling under one of the new plush couches, and start rethinking your own decor.

The Envoy Hotel, Autograph Collection
The Envoy Hotel, Autograph Collection

Get cozy with drinks on a rooftop

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 outdoor Seaport Snow Globe (rest assured that they have an indoor area as well). There are also the heated igloos atop the Lookout Rooftop at The Envoy, which have now been joined by the enclosed “ice boxes” overlooking the harbor.

Learn a new semi-obscure sport together

Seaport
Ah, curling—the sport we fall back in love with every four years during the Winter Olympics. But you don’t have to wait until Beijing—the curling lanes over at Snowport are open daily for 30-minute play slots.

Fenway
Now open Wednesday through Sunday from 10 am to 5 pm, the Museum of Fine Arts is back in action helping refined Bostonians lose themselves in world-famous exhibits. Tickets will cost you $25 per person without a membership, but only $5 on Wednesday from 3 to 4 pm. (Heads up, you’ll have to get your tickets online to facilitate limited-capacity browsing.)

North Road Farm
North Road Farm

Take a beachside horseback ride

Crane Beach
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 Robin Hood and Maid Marian vibes.

Stargaze at Coit Observatory

Fenway
Luckily for lovebirds, every Wednesday night the BU Coit Observatory opens up its facilities to all us non-scientific types 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 afterwards—especially during the dark winter months. Just don’t forget your masks, which are required for the entire show.

Embark on a walking tour of the city

Various locations
There are two ways to go: 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, it’s educational, it’s outdoors, and it’s great nerdy fun.

AstroStar/Shutterstock

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.

Coolidge Corner & Brattle Theatre
The iconic Coolidge Corner Theater is back open for business, which means you can once again enjoy first runs and midnight screenings in the flesh. And by showing your support now, you can ensure a future filled with cozy date nights and the best popcorn in town. If you’re a Red Line couple, the Brattle Theatre offers the same throwback allure.

SoWa Boston
SoWa Boston

South End
Every first Friday of the month, all year long, 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 pretend to understand what you’re looking at for hours on end.

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, snow or shine. Go forth and flex.

Ice Castles
Ice Castles

Carefully make your way through a New Hampshire Ice Castle

Woodstock, New Hampshire
Did you know there are such things as icicle farmers? And that they spend months “growing” icicles in the now-annual construction of a massive, brightly lit, interactive ice fortress? Think of it as a more romantic version of Superman's ice fortress. Weather willing, the castle will open in January.

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 as soon as the nights start getting extra crisp, the fire pits will make their comeback.

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.

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Meaghan Agnew is a contributor for Thrillist.