Downtown Rockport, Massachusetts, in winter. Image credit Micha Weber via Shutterstock

These Towns in Massachusetts Come Alive in Winter

Massachusetts is one of the most beautiful states during the winter season and prides itself on some of the best snowy and festive landscapes of the New England region. Whether one seeks an old-school Christmas scene like the one found in the wholesome holiday celebrations held in Stockbridge, the best twinkling lights that line the streets of the whole Nantucket Island, or the rare and skittish winter animals in the Stone Zoo in Stoneham, Massachusetts holds many treasure during the winter months. So, come to feel the warmth of the holiday season in these seven towns where Christmas is still celebrated the way it used to be.

Stockbridge

Christmas holiday in Stockbridge, Massachusetts
Christmas holiday in Stockbridge, Massachusetts. Image credit James Kirkikis via Shutterstock

Looking down in between the Berkshire Mountains, Stockbridge is a picture-perfect New England village that grants warmth and tranquility. With the coming of winter, tourists flock to the good old American 50s Christmas scenes depicted in Norman Rockwell's wholesome holiday paintings. Many buildings in downtown Stockbridge turn into a festive display, showcasing a sound and light spectacle for everyone to enjoy the show. The nearby Berkshire area is also great for winter sports. It provides opportunities for skiing and tubing at Ski Butternut and tubing or cross-country skiing at Hilltop Orchards. Furthermore, Hilltop Orchards also makes its own wine, so check out their selection at Furnace Brook Winery for a warming taste of great wine.

Adorable Small Towns In MassachusettsSurrounding the legendary city of Boston are dozens of small towns, including Provincetown and Rockport, the location of early Pilgrim settlement.

Rockport

Historic buildings at the waterfront of port of Rockport City in winter, Massachusetts
Historic buildings, Rockport, Massachusetts, in winter.

Only an hour north of Boston, Rockport is the perfect destination for relaxation. The strewn paths through woods and glades grant every visitor unmatched beauty and serenity. With its magical lights nearing Christmas that has inspired painters since Winslow Homer, Rockport is a welcoming seaside village. It can be a romantic getaway or a peaceful retreat for the whole family. Rockport takes Christmas seriously, though. Festivals and Christmas shows at the Shalin Liu bring the nights a new meaning as the holiday spirit permeates the air in this coastal village. Additionally, you can catch old Saint Nick coming into town on what else but a lobster boat.

Nantucket

Beautiful seaside homes in Nantucket, Massachusetts.
Seaside homes in Nantucket, Massachusetts.

Nantucket Island feels like its own little world, just a quick ferry trip away from Cape Cod. This serene island is a place to explore your sense of wonder, with the town's symbol, Brant Point Lighthouse, guiding you back to the starting point. The Nantucket Historical Association starts its annual Festival of Wreaths from the Thanksgiving week, transforming the Nantucket Whaling Museum during November and December. During the same time, the seasonal celebration kicks off in late November with the lighting of the island's Christmas trees, illuminating Main Street. This holiday event features a festive European-style marketplace with Victorian carolers, a visit from Santa via a Coast Guard cutter, and a hilarious sweater contest. Around this time, there are also plenty of opportunities to hit the ice and skate with Santa at the Nantucket Ice Community Rink.

Concord

On the Old North Bridge in winter
Old North Bridge, Concord, Massachusetts.

The town that once was the scene of the American Revolution, where the "shot heard round the world" that started the revolution occurred at the Old North Bridge, transforms into a winter wonderland during the holiday season. Concord's citizens and guests can enjoy a shopping stroll through West Concord, a Holiday Pops performance, and the town's beloved Family Tree tradition featuring over 30 decorated trees dotted around the village. Concord's historic Louisa May Alcott's Orchard House also hosts an old-fashioned Christmas celebration where visitors can enjoy music, games, and lots of decorations.

Newburyport

A Snowy Owl (Bubo scandiacus) among the beach grass on the top of a sand dune at the Parker River National Wildlife Refuge in Newburyport, Massachusetts.
A Snowy Owl at the Parker River National Wildlife Refuge in Newburyport, Massachusetts. Image credit Alan B. Schroeder via Shutterstock

Where the Merrimack River meets the Atlantic, the town of Newburyport is particularly wondrous during Christmastime. Newburyport cobblestone streets get filled with shoppers, surrounded by decorated buildings and festive lights overhead. Along with some great holiday shopping events, Newburyport also hosts a Santa parade, tree lighting, singalongs, concerts, and holiday performances. Visitors who bring the whole family also often choose the North Pole Express Train, which grants spectacular views of the surrounding snowy scenery and comes back to the Newburyport Commuter Rail Station. If you are a theater fan, visit The Actors Studio. This intimate, 50-seat theater hosts cultural events, concerts, and interactive performances throughout the year and boasts a collection of winter-themed shows to entertain and warm your heart.

Stoneham

Christmas Nativity lighted scene, snow covered front yard, Stoneham Massachusett
Christmas Nativity lighted scene, snow-covered front yard, Stoneham, Massachusetts. Image credit QualityHD via Shutterstock

Winter in Stoneham can get quite cold, with the temperatures dropping below the freezing point in December. But this does not stop tourists from coming to enjoy the plethora of events this town has to offer. If the weather is not too extreme, the main attraction of Stoneham, the Stone Zoo, is also open during winter. Visiting this comprehensive zoo, you can see snow leopards, black bears, the Arctic fox, yaks, and many others. Additionally, the Stone Zoo holds a special event during November and December and promises paths lit by thousands of twinkling lights spanning all 26 acres and a special "Santa Experience" on select nights. Another exciting event around this time is the annual Winter Arts & Crafts Fair, where more than 60 vendors sell their creations and hold some craft-your-own gift shops to prepare for the holidays.

Bradford

Winter scene of a snow covered bridge and trees In black and white in Bradford, Massachusetts
Snow-covered bridge and trees in Bradford, Massachusetts. Image credit Marie Christiane via Shutterstock

Bradford is a very popular destination for winter sports enthusiasts coming from all around the Boston area and beyond. This small suburban town is the gateway to the famous ski resort, Ski Bradford. This resort thrives with the white gold that falls down come wintertime. It provides snowboarders and skiers 48 acres of trails and terrain to explore. The Dead Hill Mountain features a vertical drop of 248 feet, boasts 15 convenient trails for all skill levels, and is serviced by ten lifts.

Most Picturesque Small Towns In MassachusettsEarly colonial settlements, swaths of Atlantic Ocean coastlines, cute capes, jaw-dropping islands, and pristine green New England scenery are the backdrops of the picturesque small towns the state of Massachusetts offers.

Traveling to Massachusetts during the winter is one of the best ways to visit a natural wonderland covered in snow. With small, close-knit communities holding heart-warming events like the annual Winter Arts & Crafts Fair in Stoneham and suburban areas featuring top-notch ski resorts like Ski Bradford resort near Boston, Massachusetts repeats history every year by attracting visitors as it did with the Pilgrims.

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Francesco Ferrante December 3 2023 in Places

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