Events

Everything You Absolutely Must Do in Boston This Winter

Updated On 01/31/2018 at 06:11PM EST Updated On 01/31/2018 at 06:11PM EST
cupid's undie run
cupid's undie run | Joseph Lee
December
Lookout Rooftop and Bar Pop-Up
Lookout Rooftop and Bar Pop-Up | Envoy Hotel
December
Thursday - Monday
Dec 21-Apr 16
Lookout Rooftop and Bar
The hotel has debuted six heated domes on its rooftop bar patio; gather up to nine of your closest drinking buddies and take in the city skyline while huddled underneath fleece blankets. As for those drinks: You merely press a button, and the igloo lights up to tell the waitstaff you’re ready for another round. Far better than real igloo residents have it.
Cost: Igloos are available on first-come, first-served basis with no fee.
Thursday - Wednesday
Dec 21-Feb 28
City Hall Plaza
If you panicked that you’d missed the boat on the plaza’s European-like Christmas market, don’t. The deadline has been extended to the end of February -- plenty of time to visit the reconfigured skating path (with DJed music every Friday night), the small-vendor market, and the traveling wine and beer exhibit.
Cost: Free admission.
Thursday - Wednesday
Dec 21-Jan 31
OAK Long Bar & Kitchen
Really, there’s no bad time to indulge in a little top-shelf bubbly -- especially when a fireplace is involved. The bar’s intimate Red Room is pouring vintage Champagnes, limited-edition whiskeys (yes, there’s Pappy Van Winkle), and top-rated reserve wines by both the half and full glasses through the end of January.
Cost: $25 for a half-pour of Dom Perignon.
January
Boston Wine Festival
Boston Wine Festival | Boston Wine Festival
January
Friday - Saturday
Jan 5-Mar 31

Apres-ski without having to ski at The Lodge at Publico

Apres-ski without having to ski at The Lodge at Publico

Publico Street Bistro and Garden
All reward, no work -- we can dig it. On Fridays and Saturdays, Publico turns its atrium into a ski lodge-like oasis with flannel blankets, squishy pillows, and even an artificial snow machine -- this on top of the fire pits and heated alcoves. The special food and drink menu includes comfort fare like hot buttered rum ($12) and a grilled cheese sandwich ($8); they’ll also be screening the Winter Olympic Games in February.
Cost: A la carte.
Saturday - Saturday
Jan 6-Mar 17
Various locations
Do you spend every winter silently seething at those car owners who can drive off to winter retreats unseen? Seethe no longer. Boston Adventures now offers two winter trips out of town: a ski bus to Sunday River on Saturdays and a night snow tubing and brewery bus to Nashoba Valley on Saturday nights.
Cost: Tickets start at $64.
Friday - Friday
Jan 12-Mar 30
Boston Harbor Hotel
This 10-week food and wine fest isn’t exactly for the light of wallet, but for those looking ahead to a wintertime birthday/anniversary/job promotion, you can’t do any better than a harborside meal celebrating a certain wine varietal or region.
Cost: Varies.
February
Cupid's Undie Run
Cupid's Undie Run | Marty McCrory
February
Thursday - Thursday
Feb 1-22
Eataly Boston
Those inhabiting The Boot spend their days on the slope to spend their evening eating and drinking. Wander amongst Eataly’s myriad counters to savor mulled wine, Aperol spritzes, and fortifying snacks like house-made sausages and cannoli aplenty. The live DJ might even cause you to forget it’s Thursday instead of Friday. It all goes down on February 1, 8, and 22, giving you three chances to savor the flavors.
Cost: $35 ticket includes three drinks and five food items.
Thursday - Sunday
Feb 1-Apr 1
Peabody Essex Museum
With unmoving cold temps comes the excuse to museum. This 125-piece exhibit is the first to display O’Keeffe’s hand-sewn clothing alongside her paintings and photographic portraits, so as to gain a deeper understanding of her overall aesthetic.  
Cost: General admission is $20.
Friday
Feb 2
Lenox Hotel
On Super Bowl weekend, it seems only appropriate to support the local arts. Lenny Clarke -- who once did 25 minutes of locker room stand-up to cheer up the ‘07 Patriots after the first Spygate headlines -- is joined by fellow Boston comedic fixture Robbie Printz.
Cost: $39.
Friday - Saturday
Feb 2-3
Seaport World Trade Center
Forget IPAs and pilsners. More than 80 brewers will be on hand to show off their strangest and strongest elixirs in an effort to bust brewski norms. If you hit the fest up on Friday, stick around the ‘hood for the Row 34 After Party.
Cost: $65 per session.
Sunday - Wednesday
Feb 4-28

Keep your winter padding intact with some Katz's Pastrami Hash

Keep your winter padding intact with some Katz's Pastrami Hash

The Butcher Shop
Wherever the Katz’s pastrami lands, we follow. The deli’s ongoing Pass the Pastrami series, which pairs celebrated chefs with the equally celebrated meat, continues with a stop at The Butcher Shop. Every Sunday in February, Barbara Lynch dishes up a decadent hash topped with poached eggs, chives, and Espelette pepper (a French spice).
Cost: $21.
Friday - Saturday
Feb 9-24
YOTEL Boston Sky Lounge Rooftop & Terrace
Dress as your favorite country, grab a Go for Gold Martini (Champagne, Belvedere vodka, lemon, lime, Life Savers), then settle into your nosebleed seats for some indoor/outdoor, sky-high Olympic viewing. (Can’t get enough of faux ski lodges and Olympics-themed food and drink? Be sure to also check out Chalet Marlowe and The Lodge at Publico.)
Cost: A la carte; overnight rooms are $123.
Friday - Sunday
Feb 9-11
Seaport World Trade Center
In a deep-winter nesting rut? It’s not too late to book a beach retreat -- or to start planning a FOMO-inducing summer sojourn. Hundreds of exhibitors clue you into trips you’ve never even considered -- and keep you lingering with their myriad prize giveaways. (Drown your sorrows in the craft beer pavilion if you don’t win anything.)
Cost: $10 in advance; $15 at the door.
Sunday
Feb 11
Copley Square Plaza
Both housed and unhoused Bostonians join together for a 2-mile walk around the city to raise funds for local homelessness organizations. Afterwards, there’s a big communal breakfast to keep the dialogue going.
Cost: Registrants commit to raising a minimum of $100; you can also donate here.
Sunday
Feb 11
Boston Public Market
It’s probably New England’s least known farm export, yet our region boasts a robust yarn scene. Meet the owners of 10 regional alpaca and sheep farms, try your hand at the spinning wheel, learn to dye your own natural yarn, then retreat to the knitting lounge for some G-rated quality time.
Cost: Free.
Wednesday
Feb 14
ImprovBoston
If you’re not part of a couple, there’s zero reason to curl up and die on Valentine’s Day. Instead, you can find the humor in heartburn as regional comics use improv, standup, song and more to relay their own personal torments.
Cost: $18.
Wednesday
Feb 14
The Automatic
This is a Valentine’s Day dinner for East Coast Grill nostalgists. Co-owner Chris Schlesinger has passed along all of his East Coast Grill Hell Night secrets to Chef Martin; “Cousin Dave” Cagle, meantime, will be making an appearance as Cupid. Hot chili-inflamed dishes are the order of the night, which basically just means aphrodisiacs galore. (There’s also a “wimp menu” for that disappointingly unadventurous date you’ll be ditching right after dinner.) And if this isn't your speed, have no fear: We have plenty of other great date ideas to entice you.
Cost: A la carte.
Friday - Monday
Feb 16-19
Montreal
Your IG friends can have their all-inclusive package island deals. Hop aboard the BSSC bus and head north to Old Montreal for shopping, skiing, snowboarding, and poutine galore. (Hitting the slopes is optional, not mandatory.)
Cost: $439-$469, hotel and transportation included.
Saturday
Feb 17
House of Blues
Don’t panic: The run itself is very “brief” (their joke, not ours), there’s a party immediately after, and you don’t even have to run in your underwear per se; an undie-related costume also works. Moreover, it’s all for a great cause: The money raised goes towards people with neurofibromatosis, or NF.
Cost: $35.
Saturday
Feb 17
Agganis Arena
Who knew West Coasters have been having all the fun? But no more: For the first time ever, the country’s largest trivia tournament has come to the East Coast. Imagine more than a thousand competitors playing for a total of $20K in prizes, all while slugging back unlimited suds. It’s a nerdy food time that also happens to benefit Artists for Humanity.
Cost: $240 per team; spectator tickets are $24.
Saturday
Feb 17
Action Kitchen at the Seaport Hotel
Because if ever there’s a month to indulge in a three-figure dinner, February is it. The “farm-to-bottle” Vermont distillery comes south to pair its small-batch whiskies with dishes like pan-roasted rabbit leg, grilled venison rib chop, and sticky toffee pudding with custard vanilla ice cream.
Cost: $150.
Saturday
Feb 24
House of Blues
It’s like an indoor summer music fest. One night, three stages, 10 bands, limitless street food, and international beers galore. World musicians this year include Rubblebucket and Mokoomba; you’ll work up such a dance sweat that you’ll barely notice the outdoor cold at the end of the night.
Cost: $48.
Tuesday
Feb 27
ONCE Somerville
You’ve almost made it to the end of the month. How to cross the finish line? An evening spent proving your Disco Stu mettle (the questions are focused on the first 10-12 seasons, thank God). Some classic episodes will be shown ahead of the question portion of the evening, and insider-joke prizes will be made throughout the evening.
Cost: Free.
March
Bourbon and Bacon Festival
Bourbon and Bacon Festival | Bourbon and Bacon Festival
March
Saturday - Monday
Mar 3-5
Seaport World Trade Center
Back nine days aren’t here again, but they will be one day. The expo includes tons of demos and interactive exhibits, plus more than 100 exhibitors hawking their wares. Take it as a further excuse to plan a springtime golf getaway.
Cost: $12.
Sunday
Mar 4
The Wilbur
Because if there’s one musical artist who can offset the world’s current insanity, Weird Al is probably the guy. Which also probably explains why the original 8pm show is already sold out months in advance. Luckily, a second 3pm show has been added.
Cost: $59-$279.
Saturday
Mar 10
The Castle at Park Plaza
Isn’t it so maddening when all the city’s best food events sell out way in advance? But this year, you can get ahead of the madness. As for the event, the name speaks for itself: two of the greatest digestible items on the planet, together at last.  
Cost: $50-$100.
Wednesday - Sunday
Mar 21-25
Brattle Theatre
We don’t yet know the lineup, but we do know this: Our annual underground film fest proves that the city’s creative class is woefully underestimated.
Cost: TBD.