Every year, we do an early winter guide around this time. And every year, without fail, readers get extremely aggravated with us about it—sometimes jokingly, sometimes not-so-jokingly. Why, they ask, would we remind Greater Bostonians about the hell that awaits?
There are a lot of answers to such inquiries, starting with the fact that some of us adore the snow and low temperatures. More importantly, though, is that icicles are inevitable, and we might as well face it. If you can’t stand the cold, then moving to Boston was a shitty decision.
With that said, we asked around the office for tips on the best way to take in the winter months. Please note: These blurbs weren’t pre-written or recommended by a publicist or paid for as tends to be the case with similar listicles you will find in other publications; they’re from the very bottom of our ice-cold hearts.
Epic sledding on the south end of the Red Line
There’s a serious sledding opportunity in Braintree that you ought to check out. Once the drifting banks roll in, you’ll want to find the town’s municipal golf course. Bundle up, pack your sleds, or even your skis if you’re feeling particularly adventurous (or don’t want to drive to a mountain), and head over to 101 Jefferson St. No reservation required, just find parking or hop in a taxi. While this spot might not be the best in Mass, it’s far less crowded than popular places in Boston like Jamaica Pond and will absolutely do the trick. Just remember that the only thing within walking distance is a Dunkin’ Donuts, so you’ll want to bring a thermos with whatever you may need to keep warm—hot chocolate, whiskey, whatever. -Jacob Schick
As winter approaches, it’s important to stay hydrated and get a good sweat on. I recommend a lot of things—Jameson, Tinder dates at the Super 88 food court in Allston, going to a restaurant like Chilipa and destroying your innards with ma la xiang guo soaked in chili oil and szechuan peppercorns. Then drink more. Now you’re shvitzing! Now you’re warm, but not quite warm enough. When you finally stop sweating, it’s time to bus it over to Chelsea, or more specifically to Dillon’s Russian Steam Bath, where Russian men will benevolently beat you with oak branches in the banya until you have nothing left to shvitz. It’s the perfect end to an ideal winter’s eve. -Daniel Kaufman
Easy ice skate and warm up in Kendall
Boston winters aren’t for the weak, you know this, but anyone who’s capable of braving the New England temperatures and snowy forecasts may be looking for a way to avoid cabin fever. Hence, ice skating. There are a lot of different ice rinks around the region, but a quaint one that doesn’t get too crowded is right in Kendall Square in Cambridge. Community ice skating there is open to the public seven days a week from mid-December to mid-March, and in addition to the usual, the rink will also hosts its annual Holiday on Ice Celebration on Dec 15, which has free admission and features a show by professional ice skaters. Put it on your calendar, and make a note to stop by Cambridge Brewing Co. to see what’s on tap. -Morgan Hume
Shop local and shop often
If you’re looking for gifts outside the door-busting realms of Target and the Apple store, local organizers have carved out a slice of non-corporate holiday cheer in Jamaica Plain. The fourth annual JP holiday flea market is the brainchild of Seek and Find, a group that focuses on free and affordable events to connect Boston’s many niche communities. On Dec 15 and 16, you can hop off the Orange Line at Stony Brook and head over to the market’s 60-plus vendors at Spontaneous Celebrations, a local event hub with similar goals of breaking down cultural barriers. In this melting pot of local artists, smiths, and repair techs (Mendi’s, a local anti-waste repair initiative, will have able hands to assist with your refurbishing needs), you’re well-equipped to find the right zine, record, or succulent cactus for you or your loved ones. While you’re there, I would recommend a Tarot reading, just to ensure you’re entering the holidays with a balanced mind and spirit. And if you’d like to put that balance to the physical test, definitely stop by the outdoor ice rink just up the street. -Sophia Higgins
Ski for free
One great thing about the tundra months in New England is that, if you have the skills or blind audacity, you can suddenly pack up a gear bag and strap your ride to your back to take on remote and ungroomed potential ski areas. Contrary to the belief of those West Coast ski snobs, there are great spots right in our collective backyard. For a proper introduction to backcountry skiing, we recommend Mount Cardigan in New Hampshire for hikes and open snowfields that will allow you the time it takes to work the basics. A bit more difficult is the John Sherburne Ski Trail in the Granite State; originally designed as an easier descent from Tuckerman Ravine, the “Sherbie” is an intermediate-level trail and has become a local favorite. While only “skinning,” a kind of hybrid between hiking and skiing, is (technically) permitted on the trail, it only takes about two hours to hike to the top. Then it’s just you and the snow, and wide-open terrain. -Dan McCarthy
Get your tube-watching setup straight
This may be obvious for some, but it still needs to be said that one way to really enjoy winter on a budget is to prepare for some unapologetic hibernation and to steer clear of typical cold sports and activities. Why bother getting dressed in an obscene amount of layers and your heaviest boots just to leave the house? Instead, stay at home, climb on some comfy furniture, kick your feet up, find a screen. The fall brought more new shows and seasons of old favorites than anyone could possibly manage to watch before winter. Come winter, they’ll all be available for streaming, plus you can expect the usual lot of Christmas and holiday specials to binge on. Call your friends, get their passwords, order up a Snuggy. When the time comes, all you’ll have to do is find the clicker. –Elvira Mora