Everything You Absolutely Must Do in Boston This Winter

Our post-Thanksgiving snowfall confirmed it: We’re back here again. No sun, no warmth, and no shorts for the next five months. So be it. There’s more than enough going on to tide us over until the first hints of spring. We have year-round rooftop drinking, we have art exhibits, we have night skiing, and we have plenty of food and drink festivals designed to shatter your New Year’s resolutions. Now all we need is some assurance that the snow and ice isn’t going to be too terrible this year. Here is everything you must do in Boston this winter.

Through Tuesday, March 31 (weather depending)
Lookout Rooftop and Bar
Yes, the igloos are back, but that’s not all. This year the hotel has added a large heated enclosure to its rooftop bar patio, which can accommodate up to 160 folks at a time and makes it that much easier to enjoy drinks like the large-format, adult hot chocolate. Meantime, the five domed, LED-lit enclosures invite up to 10 adventurers to snuggle up and enjoy the city skyline. 
Cost: Igloos are available on first-come, first-served basis with no fee

Monday, December 23 - Wednesday, April 1 (tentative)
Because winter nights shouldn’t just be about cozying up in front of the space heater. At the Blue Hills Ski Area -- accessible by public transit -- tickets after 5pm start at just $35 and still grant you four hours on the slopes thanks to the ski area’s flood lights. Maybe you won’t be cursing the next snowfall after all. 
Cost: $35-$40

Wednesday, January 1
Brattle Street Theatre
They say laughter is the best medicine for a hangover. The lineup is TBA, but expect classics like A Night at the Opera or A Day at the Races. 
Cost: $20 (tentative)

Wednesday, January 1
BCYF Curley Community Center
2020 is pretty much guaranteed to be another insane year, so might as well kick it off in a crazy way. Don a nutty costume and join the 600 or so fearless fools who plunge into the frigid Boston Harbor waters on the morning of New Year’s Day -- or just head down to watch and shake your head.
Cost: Your temporary sanity

Boston Wine Festival
Boston Wine Festival

Friday, January 10 - Friday, March 27
Boston Harbor Hotel
Now 31 years young, the 10-week food and wine fest wants you to get out of the house and enjoy yourself already. It kicks off with a grand opening reception and then moves along to special-occasion tastings and dinners, all savored harborside. None of it is cheap, but then again, seasonal affective disorder is a costly disease to beat. 
Cost: Event tickets start at $115

Thursday, January 16 - Monday, January 20
Boston Convention and Exhibit Center
It’s the perfect opportunity to leisurely investigate different makes and models without dealing with high-pressure, too-slick-by-half salespeople. And if you end up lingering a bit too long at the latest Ferrari, no one is there to judge. 
Cost: $17

Thursday, January 16 - Sunday, January 19
The Sinclair
It’s four days of local Celtic music performances without any of the attendant green beer. Discover just how deep our Celtic roots go as you enjoy songs, music, and dance reflecting the Celtic traditions of Ireland, Scotland, Cape Breton, and more. 
Cost: $10-$25

Monday, January 20
Boston Latin School
“A day on, not a day off” has been Boston Care’s motto since 2006; each year on MLK Day, the volunteer organization gathers hundreds of Bostonians for a community outreach project that honors the work of the day’s namesake. 
Cost: Free (no registration required)

Museum of Fine Arts Boston
Museum of Fine Arts Boston | Bill Damon/Flickr

Monday, January 20 - Saturday, June 20
Museum of Fine Arts
As part of a new MFA initiative, teens from several local youth empowerment organizations will curate a show of 20th century Black artists, including several Boston creatives, around the themes of “Ubuntu: I am Because You Are,” “Welcome to the City,” “Normality Facing Adversity,” and “Smile in the Dark.” 
Cost: Free with admission ($25)

Indulge in the simple pleasures of the Taste of Chocolate Festival

Friday, January 24 - Sunday, January 26
Harvard Square
There is no quicker way to happiness than free chocolate. The marquee event is Saturday’s free tasting event, 1-2 pm in Brattle Plaza -- loads of area businesses are doling out the sweet stuff to anyone who begs. But the whole weekend is about chocolate-centric deals and giveaways, guaranteed to lift you out of your late-January doldrums. 
Cost: Free

Friday, January 24 - Sunday, January 26
Mohegan Sun
Check this out because it’ll probably take you as long to fight the traffic to Encore as it will take to drive down to Connecticut for three days of wine tastings, dine-arounds, bourbon and beer events, and a little post-vino gambling.
Cost: Grand tasting is $95; a designated driver ticket is $20 

Friday, February 7 -  Monday, February 17
Somerville Theatre
The 45-year-old festival -- the longest-running genre fest in the US -- offers 11 days of escapist fare, from shorts to features to documentaries. The festival culminates in a 24-hour, noon-to-noon marathon of the good, the bad, and the unbelievably schlocky.
Cost: $90 for marathon; $175 for festival passes 

Saturday, February 9
Museum of Science
Alas, no actual dogs will be present. But you’ll come away with a nose-to-tail understanding of your favorite four-legger, from how they evolved to how they see and smell the world. You’ll even have a chance to train a virtual pup, which might just propel you to go home and finally teach Mrs. Piggle-Wiggle not to jump on the counters. 
Cost: Free with Exhibit Hall tickets ($26) 

Sunday, February 9
Copley Square 
Boston housing is the hot-button issue that’s not going away anytime soon. Join a cohort of both housed and unhoused Bostonians for a two-mile walk around the city to raise funds for local homelessness organizations. The walk begins and ends in Copley Square. Afterwards, participants gather to share breakfast and hear stories from the homeless community and from housing activists. 
Cost:Registrants commit to raising a minimum of $100, donating that amount up front, or joining a team; those who cannot walk can donate here

Cupid's Undie Run
Cupid's Undie Run

Sunday, February 8
House of Blues
Sure, there are lots of reasons not to run the city streets in your underwear in February. But the main reason you should do it: the money raised goes towards helping to find a cure for neurofibromatosis, or NF. And did we mention there’s a huge dance party immediately after? 
Cost: $30 registration fee

Tuesday, February 18 - Saturday, March 8
Huntington Theatre
Oh, we are so here for this one. The show is written, designed, and performed by the women of The Second City, who fearlessly dismantle the patriarchy through sketches and songs. Book this one now for your besties night out. 
Cost: Regular tickets start at $35

Global Arts Live
Global Arts Live

Saturday, February 22
House of Blues
You’re probably suffering from music fest withdrawal at this point. Get those juices flowing again during an indoor global music show featuring  three stages and 12 performers. 
Cost: $48 in advance 

Sunday, March 1- Friday, March 6 and Sunday, March 8 - Friday, March 13
Multiple locations
It’s an easy way to get out of your hibernation rut. The twice-annual dine around typically features more than 100 restaurants around town luring you in with prix-fixe lunches and dinners. Actual participants are TBA, but we feel hopeful that there will once again be enough newbies on the list to keep things interesting. 
Cost: Lunch $15-$25, dinner $28-$38

Saturday, March 7 - Sunday, March 8
Multiple locations
It’s an easy sell, especially for those waiting impatiently for St. Paddy’ day itself: beer, Irish music, beer, heated tents, more beer. And it presumably will be followed the next day by the annual Harpoon Shamrock Splash at M Street Beach, one of the easiest ways to shock yourself back into sobriety. 
Cost: $25 (tentative)

Wednesday, March 11 - Sunday, March 15
Seaport World Trade Center
This year’s theme is “Garden Party: Celebrating Family & Friends,” which means you’ll likely suffer from outdoor space envy after seeing all the epic backyard party setups. For those of us lacking in Newport-like lawns, there are plenty of ideas and demos around sustainable gardening, edible plantings, seed starting, indoor planting, and small-space gardening. 
Cost: $22 general admission

South Boston St. Patrick's Day Parade
South Boston St. Patrick's Day Parade

Sunday, March 15
South Boston
You know what, you know why, you know when, and you know to put out your lawn chair now. 
Cost: Free

Wednesday, March 25 - Sunday, March 29
Brattle Theatre
Discover our city’s most diverse and limitless filmmakers. The lineup is still deeply under wraps, but chances are good they’ll once more stage the Saturday Morning All-You-Can-Eat-Cereal Cartoon Party. 
Cost: $9-$12 per movie

Boston Beer and Cheese Fest
Boston Beer and Cheese Fest | Drink Craft Beer

Friday, March 27 - Saturday, March 28
Seriously, get your tickets now, because this one sells out in like January. As of right now, we’re talking 25 regional beer and cider brewers, 12 local creameries, beer and cheese pairings, and charcuterie. Did we mention that the samples are unlimited? 
Cost: $65

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Meaghan Agnew cannot believe she just wrote something about the St. Patrick’s Day parade -- she hasn’t even cleaned up from Thanksgiving yet. Track her predictable wintertime procrastination by following her on Twitter and Instagram.