Everything You Absolutely Must Do in Boston This Winter

Published On 12/01/2016 Published On 12/01/2016
Santa Speedo Run
Santa Speedo Run | Flickr/TimothyJ
Classic Harbor Line-Boston
Classic Harbor Line-Boston


Thursday - Saturday
Dec 1-31
Rowes Wharf
Let's be honest -- holiday cheer is a farce. Mostly you spend December willing away the seasonal pressures. Make your dreams a reality aboard one of the Classic Harbor Line boats. On Thursdays and Fridays throughout the month, the company offers both Christmas carol and holiday jazz cruises aboard the 1920s-style Northern Lights motor yacht. Then there's the "Cocoa & Carols" weekend holiday cruise…with hot toddies.
Friday - Tuesday
Dec 2-Feb 28
City Hall Plaza
Remember when your mom wouldn't even let you get off at the Government Center T stop? Now our government center is ground zero for everything new and exciting happening in the city. The latest installment is a European-like Christmas market with a skating path (much better than a rink), a holiday market full of local vendors, and pay-to-play attractions like Santa's House and "Vinopolis," a traveling wine exhibit.
Friday - Sunday
Dec 2-4
SoWa Power Station (540 Harrison Ave)
It's pretty much the opposite of mall shopping. Instead, you'll peruse regionally made wares from more than 100 local vendors while sipping a seasonal cocktail from Area. There's also a charity wrapping that benefits Hearth Inc., a homelessness nonprofit.
Dec 5
Island Creek Oyster Bar
By the end of the month, your imbibing will serve escapist purposes. But why not first learn to drink well? Renowned wine writer David White ( comes to Island Creek to throw an epic Champagne-fueled dinner: a five-course seafood repast paired with a selection of Champagne flights. In other words, the perfect before-Christmas couples present to give one another.  
Monday - Monday
Dec 5-12
The Hawthorne
We'll shop any holiday market located inside a bar (duh). We also respect a pop-up that dares to pop up on a Monday night. From 5-7pm on these December Monday eves, The Hawthorne lures us in with local vendors like R. Murphy Knives, Brown & Coconut, and Hearth and Harrow (and cocktails, of course).
Dec 10
Back Bay
Your Instagram game is never easier than on this day. Join the 700 scantily clad joggers whooping their way through the Back Bay; all it takes is a red hat, a Euro-style bathing suit, and a whole lot of gumption. At least all that goosebump-bringing exposure is for a good cause, specifically Play Ball Foundation, which funds sports in Boston middle schools.
Dec 13
Frank Pepe Pizzeria Napoletana
It's the one-year anniversary of the greatest pie addition to the Greater Boston area. And it's giving back, big time: one free small cheese pizza (takeout only) to all guests between 1pm and 4pm. It's well worth the drive out to Chestnut Hill.


Jan 1
Craigie on Main
It's a one-time-only reappearance of Craigie's brunch -- a great way to kick off the year, for sure. For 50 bucks you get a three-course prix fixe menu that features all the Craigie classics. But it gets better: One lucky table, chosen at random, gets all their meals comped. That's what we call a no-lose gamble.
Jan 28
House of Blues
Three stages, 10 bands, and limitless street food and drink (insofar as you can limitlessly stuff your gullet). The House of Blues indoor music fest spotlights world music from the likes of Daby Touré and Debo Band and pretty much demands you hit the dance floor (wallflowers can take a seat in the balcony).
Tuesday - Sunday
Jan 31-Feb 12
Boston Opera House
What with Hamilton still an all-ages sensation and La La Land an awards-season favorite, it’s safe to say that musicals are back. So just line up behind the masses already and spring for tix to the Sam Mendes/Rob Marshall sensation. And just be honest: You already know all the words to "Cabaret" and "Willkommen" already.
Boston Wine Expo
Boston Wine Expo


Saturday - Sunday
Feb 18-19
Seaport World Trade Center
Your 2017 resolution: Learn what the hell you're talking about when you talk about wine. We suggest doing it crash-course style at the city’s biggest vino gala. Hundreds of exhibitors will wet your whistle; once you've gotten good and loosened up, you can spring for one of the deeper-dive seminars. And if you already know what the hell you're talking about, there's always the Vintners' Reserve Lounge, where you can sample all the rarest and most expensive bottles.
Feb 26
Back Bay Events Center
Celebrate your Jewish roots, or celebrate the Jewish roots of others. Either way, you're eating like a kinig. More than a dozen local restaurants (Juliet, Hojoko) will show off their highfalutin takes on traditional fare, while regional brewers (Notch, Bantam Cider) offer a considerable upgrade from Manischewitz.
golf expo


Friday - Sunday
Mar 3-5
Seaport World Trade Center
It's time to remind yourself that there are plenty of back-nine days ahead. The World Trade Center expo includes tons of demos and interactive exhibits, plus more than 100 exhibitors hawking their wares. Just beware: With months of cold weather bearing down on your shoulders, you might be an easy target.