12 Ways to Love Winter in Massachusetts

From après-sea to après-ski, options in the Bay State abound.

By Yankee Staff

Jan 22 2023


Located in Western Massachusetts, in the Berkshires town of Hancock, Jiminy Peak Mountain Resort is the largest ski and snowboard resort in southern New England.

Photo Credit : Massachusetts Office of Travel and Tourism

Sponsored by the Massachusetts Office of Travel and Tourism

Nicknamed “the Bay State,” Massachusetts is famed for its beautiful, 1,500-mile Atlantic coastline, where water meets land in truly magical ways. But when temperatures drop, water meets land across the Commonwealth in the form of sparkling frost and gleaming snow, spreading the spirit of winter enchantment from Cape Cod in the east to the Berkshires in the west.

If you’ve visited Massachusetts only in summer or fall, you haven’t gotten the full picture of this geographically diverse, fun-filled part of the country. Massachusetts has a strong pedigree as a winter wonderland: It boasts one of the oldest ski areas in the U.S. (Bousquet, founded in 1932), the largest tubing park in New England (Nashoba Valley), and an outdoor skating rink that’s been voted the best in the nation by USA Today (the Boston Common Frog Pond). Not to mention, it’s been a training ground for decades for top skiers, skaters, and other winter athletes, with Massachusetts natives bringing home no fewer than 18 gold medals in the Winter Olympics — the third-highest total among all 50 states.

Yet winter fun here isn’t all about zipping down the slopes or hitting the ice. There are plenty of cozy comforts to mix in before or after any outdoor adventure. Drawing inspiration from the Bay State’s six distinctly different tourism regions, here are a dozen ideas to get you started on building the perfect winter getaway in Massachusetts.


Ice skating on the Worcester Common Oval is a classic winter activity that’s family-friendly and affordable — kids 5 and younger can even skate free!

A favorite winter destination in Central Massachusetts can be found in New England’s second-largest city, as Ice Skating on the Oval welcomes visitors of all abilities to glide and spin in the heart of downtown. Opened in 2012, the 12,000-square-foot rink is even bigger than the one at New York City’s Rockefeller Center. In addition to skate rentals there are concessions, music, and special events such as the Downtown Worcester Winter Festival (Feb. 4) and a Valentine’s Day Skate Day (Feb. 12). Other favorite skating spots include:Boston Common Frog Pond, Boston; MarketStreet Rink, Lynnfield; Winter Skate at Patriot Place (returning in 2023-2024), Foxborough.


In addition to offering lessons, rentals, skiing, and snowboarding, Westford’s Nashoba Valley Ski Area is a magnet for snow tubing fans thanks to its nearby tubing park in Littleton, the biggest and best facility of its kind in New England.

Whether you’re an experienced skier or snowboarder or just getting started, Massachusetts has the perfect slopes for you. A number of the state’s 11 ski areas can be found in the mountains of Western Massachusetts‚ including Jiminy Peak Mountain Resort, southern New England’s largest full-service ski resort. But to experience New England’s largest tubing park, head to the North of Boston region, where Nashoba Valley Ski Area beckons with up to 16 lanes of all-ages exhilaration. Other favorite ski areas include:Wachusett Mountain, Princeton; Ski Butternut, Great Barrington; Blue Hills Ski Area, Canton; Catamount Mountain Resort, Egremont; Berkshire East Mountain Resort, Charlemont; Ski Bradford, Bradford; Ski Ward, Shrewsbury.


Looking to put a new spin on your hot cocoa fix? Located next to the famed Peabody Essex Museum in Salem, Kakawa Chocolate House specializes in what it calls “drinking chocolate elixirs” that draw on historic recipes across a variety of cultures.

A favored stop for many North of Boston visitors, the history-rich city of Salem offers not only top-notch museums and cultural sites but also some of the finest hot chocolate in the Northeast. Stop into Kakawa Chocolate House, which opened here in late 2018, to sample an intoxicating menu of hot chocolate “elixirs” inspired by Mayan, Aztec, and historic European and Colonial American recipes. Other hot chocolate pros include: L.A. Burdick, Boston and Cambridge; Hot Chocolate Sparrow, Orleans, Chocolate Springs Café, Lenox


Even four-legged friends can get in on the fun of cross-country skiing, as seen in this winter snapshot from Hampshire County in Western Massachusetts.

If you’re dreaming of the kinds of winter scenes that New England artists have long painted, then consider visiting the Berkshires region of Western Massachusetts, where snow’s arrival is a crisp white invitation to explore picturesque fields and woodlands. At Notchview, a 3,100-acre property in Windsor owned by The Trustees, you’ll find trails groomed for classic cross-country and skate skiing, backcountry terrain to snowshoe, and equipment rentals available. And for a once-in-a-lifetime winter outing, pay a visit to Hilltop Orchards in Richmond, and set out on snowshoeing and winter hiking paths designed by world-renowned trail architect John Morton. You’ll have wide-open views that stretch into three states if you reach the top of the hill, and a crackling wood fire, artisanal hard ciders, wines, and fresh-made cider doughnuts awaiting your return. Other cross-country/snowshoeing destinations include:Great Brook Ski Touring Center, Carlisle; Weston Ski Track, Weston; Canterbury Farm, Becket; Northfield Mountain, Northfield.


The Jim Dine sculpture “Two Big Black Hearts” draws an admiring group of art lovers at Lincoln’s deCordova Sculpture Park and Museum, which is one of the more than 100 special places across Massachusetts that are owned by The Trustees.

In Greater Boston, you can commune with nature and art against a snow-dusted backdrop at the deCordova Sculpture Park and Museum in Lincoln, where some 60 works by notable 20th- and 21st-century artists are on display year-round across 30 rolling acres (bring your own snowshoes for maximum fun). Or head to the mountains of Western Massachusetts to explore The Clark’s 140-acre campus in Williamstown. Tuesdays through Sundays, you can borrow snowshoes for an outdoor adventure, then step indoors to warm your toes and feast your eyes with a slow stroll through the galleries — admission is free January through March. Other art-full destinations include:Fuller Craft Museum, Brockton; Dr. Seuss National Memorial Sculpture Garden, Springfield; Mass MoCA, North Adams.


Rustic stone walls, plush chaise lounges, and soft glowing lights set the scene for relaxation in the resting area at Mirbeau Inn & Spa in Plymouth.

When the weather outside is frightful, a spa can restore your sunny outlook with warm whirlpools and soothing massages, among other pampering pleasures. South of Boston, the historic town of Plymouth hosts the award-winning Mirbeau Inn & Spa, which offers a 16,500-square-foot oasis where you can relax with your feet in a heated massage pool, meditate in a eucalyptus-infused steam room, or even enjoy a glass of wine by a cozy fireplace. Other hotel spa standouts include:Canyon Ranch, Lenox; Chatham Bars Inn, Chatham; Dan’l Webster Inn & Spa, Sandwich; Encore Boston Harbor, Boston; Mandarin Oriental, Boston.


Winter offers a time to slow down and explore beaches that are typically bustling in summer, such as South Beach (Katama Beach) in Edgartown on Martha’s Vineyard.

Scattered across the Massachusetts coastline are picturesque coves and beaches that may be crowd favorites in summer, but feel like private paradises in winter. Take Chatham’s Lighthouse Beach, in the Cape & Islands region, a lovely bit of sand that you’ll probably have all to yourself as you walk the ever-changing tideline to see what the ocean has delivered. Even better, if you park in the overlook lot, you can stay warm in your car and watch the sunset until the pink streaks turn to indigo. Other winter beach retreats include:Parker River National Wildlife Refuge, Newburyport; Crane Beach on the Crane Estate, Ipswich; Sconset Beach, Nantucket; South Beach (Katama Beach), Edgartown, Martha’s Vineyard; Cape Cod National Seashore.


Ocean Edge Resort & Golf Club, an AAA Four Diamond property in Brewster, offers private heated igloos for the experience of dining amid a winter sunset.

The alfresco winter dining options that sprouted up across Massachusetts during the pandemic era may be less numerous these days, but some were such hits that they have returned season after season. Those instantly classic “igloos” can be found just about everywhere, including Ocean Edge Resort & Golf Club in Brewster: At this Cape & Islands regional favorite, diners relax in sparkling geodesic domes that are part of the resort’s pop-up Frost Bar. Other igloo-dining venues include:Lock 50, Worcester; 75 on Liberty Wharf, Boston; Inn at Hastings Park, Lexington; Mile Marker One, Gloucester.


The old-fashioned delight of a sleigh ride complements deliciously authentic Colonial food during the seasonal “Fireplace Feast” dinners at Salem Cross Inn in West Brookfield.

Drink in snowy views and nostalgic vibes when you take a sleigh or wagon ride through the Central Massachusetts woods at Cornerstone Ranch in Princeton, which sweetens the experience with hot chocolate and s’mores around a campfire. For a truly immersive outing, head to West Brookfield’s venerable Salem Cross Inn for the “Fireplace Feast”: an 18th-century-style dinner paired with a horse-drawn sleigh or wagon ride over the inn’s pristine 600 acres. Also look for: Old Sturbridge Village, Sturbridge.


Throughout the year, The Trustees offers opportunities to explore several of its properties by the light of the moon — an experience that can be especially memorable amid the sparkling stillness of a winter night. Here, a brilliant supermoon rises over the dunes of Crane Beach.

Come see winter in a whole new light with The Trustees, the oldest regional land trust in the world and a tireless advocate for the rewards of getting out into the natural beauty of Massachusetts. The group hosts guided full-moon hikes throughout the year, including at the Crane Estate in Ipswich, and World’s End in Hingham. As the sun sets and the moon rises, you’ll stroll a pristine landscape as your guide shares lunar lore as well as the history of the property. Additional Trustees properties with full-moon hikes:Appleton Farms, Hamilton/Ipswich; Chestnut Hill Farm, Southborough; Fruitlands Museum, Harvard.


In addition to creating tasty products for retail sales, a number of Massachusetts sugarhouses serve up their sweet harvest to the public during hearty on-site breakfasts.

There are few sights as stirring as a sugar shack in full swing on a blue-sky day in late winter; clouds of steam billowing out of the shack’s roof seem to crack open the door to spring. March is officially designated as Massachusetts Maple Month in the Commonwealth, so make the most of this sweet season with breakfast at a Massachusetts sugarhouse like High Hopes Farm in Worthington, in Western Massachusetts, where you can feast on bacon, eggs, sausage, ham, and pancakes and French toast drenched in syrup fresh from the boiler. Other sugarhouse breakfast spots include:North Hadley Sugar Shack, Hadley; Steve’s Sugar Shack, Westhampton.


Left: The “Rockin’ Chair” cocktail (black tea-infused bourbon, ginger cognac, and lemon) at Trina’s Starlite Lounge in Somerville. Right: A selection of cold-weather cocktails (“French Bandito,” “Blizzard of ’78,” and “Ole’ Man Winter”) at the Bowery Bar in Dorchester.

No matter how you’ve filled up your perfect winter day — strolling a quiet beach, zipping down a ski mountain — there are few finales that can equal a warm-you-up-from-within cocktail or mocktail at one of Massachusetts’s cozy and inviting bars and lounges, especially when paired with a bit of tasty food. For instance, you’ll find no shortage of hot toddies, spiked hot chocolate, and other delights in Greater Boston, where you can order a “Sweater Weather” at Back Bay Social, an “Ole’ Man Winter” at The Bowery Bar, or a “Hot Rockin’ Chair” at Trina’s Starlite Lounge. If you’re more of a beer lover, stop into a local favorite like Cambridge Brewing Company or Night Shift Lovejoy Wharf for classic pub fare and handcrafted brews. Other cocktail spots and brewpubs include:Mahoney’s Atlantic Bar & Grill, Orleans; Bar 25, Newburyport; District Kitchen & Bar, Pittsfield; Northampton Brewery, Northampton; Cisco Brewers Kitchen & Bar, New Bedford