February 2025: Looking for the best things to do this winter in Boston? The New England city shines this time of year with must-see museum exhibits and bountiful comfort food (best enjoyed by an atmospheric fireplace).
Fall in New England is iconic—but for many people, that means getting out of the city. Boston in winter is downright dreamy, however, and there's tons of stuff to do. Students are back in full force and comedy clubs, college bars and music venues are at full strength. Our on-the-ground editor and writers traverse the metro area looking for the best of the best to curate this ultimate guide to things to do in Boston each month. So plan your itinerary and enjoy peak Boston this winter.
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Even to our fellow New Englanders, Bostonians can sometimes sound like we are speaking a different language. Whether you’re a college student with four years ahead of you, you just married a local or are simply here for a vacation, everyone new to Boston could use a crash course on our local lingo. From our colorful terms of endearment to the nicknames we’ve bestowed upon our favorite neighborhoods, there’s so much more to Boston slang than dropping your “Rs.” So, when you ask for directions to the Freedom Trail or to the best Irish pub in town, listen carefully and you may be able to translate a few of our favorite Boston sayings.
Bang a uey (v.): to make a U-turn, likely an illegal one because that’s just how we do.
Bubbler (n.): a drinking fountain.
B’daydas (n.): a term of endearment for potatoes.
The Cape (n.): Cape Cod, where tourists and preppies flock during the summer months, causing hours of traffic delays south of the city.
Carriage (n.): a shopping cart that you use to get your groceries, most likely at Market Basket.
Cellar (n.): the basement; pronounced “cell-ah.”
The Charles (n.): The Charles River, which is no longer flowing with its infamous “dirty water”... but you should still probably close your mouth ASAP, if you ever fall in.
Clicker (n.): the remote control; pronounced “click-ah.”
Coogans (n.): where you get dollar drafts.
Comm Ave (n.): no one has time to say Commonwealth Avenue.
Dollar Drafts (n.): see Coogans.
Dungarees (n.): jeans...
Whether you follow the rainbow to an early St. Patrick's celebration, sit in awe at an inclusive dance studio's touching performance, or you put on your best judge hat and decide who makes the best chili or the best laughs, there is certainly no shortage of things to do in Boston. We have some ideas for the best things to do this weekend in Boston.
RECOMMENDED: Full guide to the best things to do in Boston
Maybe it’s the history, rooted in the wild 1920s, behind speakeasies that make them seem so romantic and mysterious. Or maybe it’s the feeling of doing something a little bit naughty (even though Prohibition ended back in 1933) by knocking on a secret door and knowing a password. Whatever the reason, we love a good speakeasy! Luckily, our city has quite a number of discreet spots that serve legal drinks while replicating that speakeasy vibe. Below, find our guide to the best basements, nooks and hidden spots that welcome in-the-know imbibers.
RECOMMENDED: See the full list of the best bars in Boston
Navigating Boston's labyrinthine streets can be daunting, looking for hidden gems waiting to be unearthed. But fear not—we know where to find these undercover spots. From cozy cocktail lounges nestled in secretive alleyways to a supply closet-turned immersive restaurant experience, we unveil the top-notch eateries and cocktail experiences just waiting to be discovered in Boston.
Want to make a weekend of it? Get a room at one of the best hotels in Boston and follow up with one of the best brunches in the morning.
Where should I eat in Boston? is a question the editor and writers at Time Out Boston get a lot. The best answers take into account the occasion, vibe and even time of year for what you’re looking for—maybe it’s a cozy fireplace or wine bar this fall?
RECOMMENDED: Boston’s best bars
Choosing where you should eat right now is the way we like to look at it, as we compile our list of Boston’s best restaurants each season. From casual choices for seafood, pizza and wine-friendly small plates to occasion-worthy celebrations of seasonal cuisine, each of these places is a draw for its own reason. To compare them is literally apples to oranges sometimes, but we rank it anyway. Comprising restaurants we want to return to again and again, here are 30 best restaurants to book in Boston right now.
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We all know that Boston’s best fine dining spots and most romantic restaurants can stand up to those of bigger cities like NYC and London. But sometimes we just don’t get the same level of recognition as those cities. Regardless, we know that lots of spots in town deserve the same level of hype so we have rounded up all our favorites that we would recommend for a Michelin star if the guide ever does come to town.
RECOMMENDED: Full guide to the best restaurants in Boston
The North Shore has many draws, from its beautiful beaches and whale watches to scenic and historical sites. The expansive region is also home to excellent restaurants, some even rivaling Boston’s best. Shaped by the fishing industry and proximity between southern New England and Maine, Cape Ann and the North Shore boasts impeccable seafood, regional specialties and spots with citified appeal. Whether you’re planning a day trip, weekend away or longer stay on the North Shore, here’s where to eat right now.
Hecate is the coolest new bar that has opened in Boston proper in the past few years. Owned and operated by the same team behind Krasi, this underground speakeasy feels as if it belongs in New York City, rather than Boston in the best way. As you enter, your eyes slowly adjust to the darkness and the bartenders, who are referred to as your “spirit guides” whip up the stylish drinks in the background as you wonder who else has managed to snag a table at the coolest spot in town.
While many of us could easily spend every waking moment in Boston, it can be refreshing to escape the city for 24 hours or so. Fortunately, this picturesque New England region offers an array of potential day trips from Boston, including quaint seaside villages, historic towns and stunning mountain vistas. So grab your pals or significant other, and hop on a ferry, train or automobile to one of these lovely destinations. Once you're back in town, you'll once again feel ready to take advantage of the best Boston attractions, best free things to do in Boston and best museums in Boston. And when you need a little longer time away check out our list of the best weekend getaways in New England.RECOMMENDED: The Best Hotels in Boston