37 Ways to Have Fun All Winter Long in Boston

Bone-chilling temps be damned. From hitting the region’s most spectacular slopes to gliding around an ice rink with the kiddos and treating yourself to a much-needed spa day, here are 37 ways to embrace New England’s toughest season—and have a rollicking good time doing it.

Edited by Brittany Jasnoff and Andrea Timpano

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Photo via Art Phaneuf/Alamy Stock Photo


The only thing more exciting than the season’s first snow? Getting outside to play in it. By Jonathan Soroff

Hit the Slopes

Make fresh tracks at some of New England’s most popular mountains.

Wachusett Mountain
Number of trails: 27
Elevation: 2,006 feet
Miles from Boston: 53

Why go? So what if it’s a little dinky compared to other mountains? It’s only an hour away, and sometimes you just want to get a few runs in without an overnight. (As the advertising earworm succinctly puts it, “Wa-Wa-Wachusett…mountain skiing, minutes away.”) Bonus points for the equipment tune-ups on the Big Blue Zoom machine, so you won’t waste time or money when you finally do jet off to Aspen.

Lift tickets start at $44, wachusett.com.

Bretton Woods
New Hampshire
Number of trails: 98
Elevation: 3,100 feet
Miles from Boston: 156

Why go? Owned and operated by the Omni Mount Washington Resort, the mountain welcomes skiers of all abilities with plenty of terrain, unbeatable views of the Presidential Range, and a new, three-tiered lodge featuring two restaurants at the summit. As for the hotel, the grand Gilded Age edifice was the birthplace of the World Bank, but an even better financial reason to stay there is that guests receive discounted lift tickets, as well as access to other amenities such as the basement bowling alley.

Lift tickets start at $85, brettonwoods.com.

Photo via Comstock Images/Getty Images

Number of trails: 122
Elevation: 3,625 feet
Miles from Boston: 205

Why go? People call it “the Vail of the East,” but this resort is arguably even prettier than its Colorado counterpart (not that we’re biased!). Spruce Peak caters to beginners, but even the most extreme adrenaline junky will find plenty of thrills. The truly hard-core can try Teardrop Trail, an off-piste, 2-mile run that requires skinning up the mountain, while the more sedentary can skip the slopes altogether and explore shops around town. To switch things up, try cross-country skiing at nearby Trapp Family Lodge, the first Nordic ski center in the nation.

Lift tickets start at $114, gostowe.com.

Carrabassett Valley, Maine
Number of trails: 162
Elevation: 4,237 feet
Miles from Boston: 223

Why go? If you haven’t made the trek up north to Sugarloaf in a while, you may be pleasantly surprised. Since 2010, the resort has added 600 acres of terrain, while new trails and high-speed lifts are under way. What’s more, it boasts New England’s only true cat skiing (back-country courses accessible via snowcats), and its signature Snowfields offer the only lift-serviced, above-tree-line slopes in the East. When it’s time to take a break from the action, unwind with elevated pub fare at 45 North, set inside the base lodge, or stroll the scenic streets of nearby town Kingfield, which oozes New England charm.

Lift tickets start at $31, sugarloaf.com.

Photo via Dolgachov/Getty Images

Don’t Like to Ski? 

Try one of these snowy adventures instead.


What could be better than a sunny winter day spent ambling through pristine powder? Marvel at the beauty of nature blanketed in white along scenic trails at several Trustees properties across the region, including Appleton Farms in Ipswich and Hamilton (which also offers equipment rentals) and Francis William Bird Park in Walpole.

Snow Tubing

The beauty of hurtling yourself down a slope on an innertube is that it requires absolutely no skill and only a modicum of courage. With 18 lanes and four lifts, the wait times are never too long at Nashoba Valley Ski Area in Littleton. Cranmore Mountain Resort in North Conway, New Hampshire, meanwhile, also offers a mountain coaster, swing ride, and zipline, should you find yourself feeling like a daredevil.


Looking to get Fido involved? Skijoring is Norwegian for cross-country skiing with an assist from a four-legged friend (horses and snowmobiles can also be used). To try it out, head to Outdoor Center at Gunstock Mountain Resort, in Gilford, New Hampshire, which offers skijoring instruction for newbies.

Illustration by Peter Sucheski

How To …

Survive a Night in the Frigid Backwoods

You’re skiing off-piste and get lost. How do you make it through till morning? Jeff Hatch, founder and lead instructor at the Raven Wilderness School in Williamsburg, offers the following tips.

Erect a shelter.

To build a shelter, use a natural structure, such as a rock or a fallen tree. Leaves or live branches can also be helpful—especially boughs with needles, which you should lay on the ground to use as insulation. “There’s plenty to work with out there,” the instructor notes.

Photo via Coprid/Getty Images

Start a fire.

Make sure it’s close to or inside your shelter to help maintain your core temperature, which is key to survival. “Even in winter, there’s dry kindling around,” Hatch says. “The lower branches of a conifer tree, such as a spruce or a hemlock, are ideal.” The pro also recommends building a signal fire, separate from your shelter fire, to attract help. Construct a tepee configuration with dry materials such as birch bark inside, and live, green boughs (which produce lots of attention-grabbing smoke) outside.

Make your own H2O.

You can survive for a long time without food, but not without water. “Melt snow, or boil water from a stream,” Hatch suggests.

Photo via MediaNews Group/Boston Herald via Getty Images


When Boston freezes over, warm up with a romp outdoors. By Madeline Bilis

Get in the Rink

Lace ’em up tight and prepare to glide like you’ve never glided before.

Boston Common Frog Pond

Best for: Bostonians anxious to revive their Before Times traditions. While the Frog Pond was closed to skaters last year, this winter promises all the magic of years past, and then some.

How much it’ll cost: Anyone over 4-foot-10 pays $6 to get on the rink. Skate rentals are $12 for adults and $6 for kids, while lockers are an extra $5.

Coolest feature: “Bobby the Skating Seal,” which you can rent for little ones to sit on or push along the ice to help keep them on two feet.

Jack Kirrane Ice Skating Rink

Best for: Athletes young and old. Located inside Larz Anderson Park, this Brookline go-to offers informal drop-in hockey for adults, plus leagues for men and kids.

How much it’ll cost: Daily tickets run between $5 and $9, depending on your age and whether you’re a resident of Brookline. Figure- and hockey-skate rentals are $7 for all.

Coolest feature: Classes for newbies, taught by pros from Bay State Skating School. Sign up for a 50-minute session, and you’ll be cruising with ease in no time.

Skate @ Canal District Kendall

Best for: Casual skaters looking for a quick spin around the rink. Located in the Canal District, this cool spot offers an easy on-and-off experience. And if you don’t want to lug your skates on the T, parking’s available in the Kendall Square South Garage.

How much it’ll cost: Adult tickets are $5, while children’s tickets are $3. Figure-skate or hockey-skate rentals are $8 for adults and $5 for kids.

Coolest feature: Unlimited season passes. With discounts for seniors and college students, they ensure fun workouts all winter long.

Winter Skate at Patriot Place

Best for: Families making a day of it. Venture to Gillette Stadium in Foxboro, where the Winter Skate rink is steps from other cold-weather-friendly attractions including a bowling alley and Top Golf.

How much it’ll cost: Adult admission is $10. Kids 12 and under, as well as seniors 65 and older, pay $6. Skate rentals for everyone are $5.

Coolest feature: The observation deck by the rink, where you can spectate from the sidelines with a warm drink in hand.

Photo by Soren Hald

Chase a New High

You’ve seen kiteboarders, right? Fearless riders who splash across the waves while gripping the line of a high-flying kite? Swap the ocean for a frozen lake (and the kite board for a snowboard or a pair of skis), and you’ve got the makings of a snow-kiting sesh. Here’s where to go when you’re ready to fly.

Lake Sunapee
New Hampshire

At almost 1,100 feet above sea level, this Granite State lake freezes faster than other bodies of water in the region. It also ensures plenty of wide-open space for extended runs: The lake stretches 8 miles long and 2.5 miles wide.

Lake Quannapowitt

For a spot closer to home, grab a trainer kite at the REI in Reading, then drive a mere three minutes to Lake Quannapowitt in Wakefield. Just be sure the ice is at least 5 inches thick before setting up.

Lake Mascuppic

Got a couple of ice fishers in your crew? Have them set up their rods at this lake near the border of New Hampshire while you catch air with your kite. Take off from the lake’s boat launch in Dracut or from Tyngsboro town beach for a crowd-pleasing afternoon.

Photo via Vspn24/Getty Images

How To …

Chip That Ice Off Your Driveway Without Breaking Your Neck

Leave the slipping and sliding for the real ice rinks.

Illustration by Peter Sucheski

Plan ahead.

Go to your hardware store now. Like, right now. Buy some salt and a big bucket to store it in, then place it near your front door, recommends Wills Mahoney, cofounder of Plowz & Mowz, an on-demand snow-plowing app that services Boston. That way, you’ll be ready to spread it on your driveway or sidewalk ahead of a storm or a cold snap. “It is best to be proactive before the ice begins to accumulate and makes it harder to remove,” Mahoney says.

Get the right gear.

“Some people use sand to ward off ice, and it’s not nearly as effective,” Mahoney says. When selecting salt, he says to go for Safe Step, a relatively inexpensive option sold in most hardware stores that gets the job done down to 5 degrees. You’ll also want to wear the right clothing—don’t just waddle out there in New Balances and a fleece. Pull on some wool socks, layer up, and take breaks when needed to prevent the risk of a heart attack, Mahoney says.

Attack from all angles.

Already stuck with an ice rink for a driveway? Start damage control by removing any snow off the ice and laying down salt as soon as possible. Then, break the ice into large chunks with a posthole digger, Mahoney says. Finally, scrape it away with a flat shovel.

Photo by Michael Diskin Assembly Design Studio


Not into bundling up? Ditch the parka and find your happy place inside these city hot spots. By Simone Migliori

Feel the Heat

Four fireside hearths to keep you cozy when the temperature drops.

Night Shift Brewing Everett Taproom

Type of fireplace: Gas
Number of fireside seats: A five-person round table plus an eight-person bar in a relaxed atmosphere.

What to order: Grab dinner from a rotating lineup of local food trucks, then order a pint of Tough Cookie, a seasonal gingerbread stout brewed with brown sugar and spices. If beer isn’t your thing, opt instead for the holiday version of Night Shift’s popular Hoot hard seltzer, festively flavored with honey, cherries, ginger, cinnamon, orange peel, and spruce tips.

Capo Restaurant and Supper Club
South Boston

Type of fireplace: Wood-burning
Number of fireside seats: Four eight-person round tables, made from reclaimed northern hard pine. Already running hot? Snag a view of the fire from a comfortable distance at the 20-seat bar.

What to order: The flames continue on the menu, which—starting this month—will feature wood-fired dishes cooked on Capo’s forthcoming custom grill, including Wagyu steak skewers and citrusy rotisserie chicken. Wash it all down with beverage manager Jess Devlin’s new cocktail That Smoke Is Fire, a mezcal negroni sour.

Photo by Michael Kleinberg

Avery Bar at the Ritz-Carlton, Boston

Type of fireplace: Gas
Number of fireside seats: Two four-person banquettes and four chairs in a luxe living room–style space.

What to order: Sip on mixologist Sterling Jackson’s Smokey Skies, made with vodka, a scotch wash, and burnt orange, while you kick back and relax in the recently remodeled lounge on a cold winter evening. And don’t forget to bring a friend to sample treats from chef Kenneth “Shane” Cooprider’s sharing-friendly winter menu, including the melt-in-your-mouth Moulard duck, served with black truffle foie gras torchon and a croissant waffle.

Grill 23 & Bar
Back Bay

Type of fireplace: Gas
Number of fireside seats: One four-top and a pair of two-tops, tucked away in the second-floor dining room.

What to order: Frosty weather is no match for a piping-hot bowl of French onion soup, followed by Grill 23’s savory gnocchi Bolognese or filet mignon. Toast to a good meal with a cheeky Death & Taxes cocktail—made with cigar-infused Larceny bourbon, peach syrup, lemon juice, and Fernet-Branca—or a full-bodied cabernet from the award-winning collection of wines.

Photo courtesy of One Dalton/Four Seasons Boston

To the Spa!

Because when it’s cold, dark, and gray outside, you deserve some pampering inside.

“Smooth, Sculpt, Soothe” facial
The Wellness Floor at One Dalton

Gear up for winter’s cool, drying air with a fortifying skin treatment. Created to calm your mind while alleviating skin irritation, this newly introduced facial combines a rose-quartz stone massage with innovative formulas such as pure gold, niacinamide, and hexapeptide to lift, firm, and sculpt the complexion.

“Warmth and Wellness” body treatment
The Spa at Mandarin Oriental, Boston

Want to vanquish the stress of the holiday season in about two hours? Make an appointment for this relaxing service, which starts with a head-to-toe dry-brush exfoliation, followed by a heated body wrap featuring fatigue-busting muscle gels and warming muds to detoxify and renew your skin. Finish with a series of hydrating creams, plus a scalp and pressure-point facial massage.

“DiamondGlow” facial
The Men’s Den

Take note, guys: Spa days aren’t just for women. This facial at the Men’s Den, a brand-new Newton spa, is tailored to the unique needs of the male visage. Performed with a patented diamond-tip wand, the treatment provides deep exfoliation—perfect for rougher skin textures and those who don’t regularly follow a skin-care regimen.

Photo via Diana Miller/Getty Images

How To …

Make the Perfect Cup of Cocoa

Craving a mug of homemade hot chocolate? Cook’s Illustrated editor in chief Dan Souza has just the recipe for a better-than-store-bought mix to keep on hand all winter long.

Illustration by Peter Sucheski

1. Add 1 cup of sugar, 6 ounces of finely chopped unsweetened chocolate, 1 cup of unsweetened cocoa powder, 1/2 cup of nonfat dry milk powder, 5 teaspoons of cornstarch, 1 teaspoon of vanilla extract, and 3/4 teaspoon of kosher salt to a food processor. Blend for 30 seconds to a minute, or until the ingredients are ground down into a fine powder. Tip: Try subbing in mint extract instead of vanilla for a fresh twist, or add 1/3 cup of instant espresso powder for a mocha variation.

2. Transfer the mix, which makes 12 one-cup servings, into an airtight container. Store at room temperature for up to two months.

3. In a saucepan over medium heat, warm 1 cup of whole, one percent, or 2 percent milk until the milk steams and bubbles appear around the edges.

4. Add 1/4 cup of the hot chocolate mix to the milk and whisk constantly for two to three minutes while the milk simmers.

5. Carefully transfer the hot chocolate into your favorite mug and enjoy!