7 Best New England Christmas Towns

By Lisa Medeiros Nov. 21, 2021
(Credit: caniaphotography/Shutterstock)

From the enchanting cobblestone streets to the gilded-age mansions, New England is a magical place to visit year-round. But the winter holidays hold a special allure. With festive activities like horse-drawn carriage rides, tree lighting ceremonies and visits with Santa, this part of the country has something for everyone. We’ve put together a list of the seven best New England Christmas towns to help you start your holidays off right.

Kennebunkport, Maine

Christmas
7 Best New England Christmas Towns: Kennebunkport, Maine (Credit: Danita Delimont/Shutterstock)

The quaint seaside town of Kennebunkport carries that coastal vibe into their Christmas celebration during Christmas Prelude. During the first two weeks of December, this historic shipbuilding and fishing village comes alive with holiday spirit like only Maine can deliver. The event’s main attraction is Santa’s arrival via lobster boat, accompanied by his lobster elves. In addition to Santa’s unique entrance, the celebration includes a tree lighting, a Christmas market, caroling and plenty of spiked cider.

Newport, Rhode Island

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7 Best New England Christmas Towns: Newport, Rhode Island (Credit: Dan Hanscom/Shutterstock)

Dubbed The Classic Coast, Newport attracts visitors year-round with its scenic seaport and opulent mansions. And Christmastime is no exception. From mid-November through December, visitors can tour Marble House and The Elm mansions, all decked out for the holidays. But the main attraction is The Breakers, where guests are greeted by a 15-foot tall poinsettia tree in the Great Hall. The Breakers hosts Sparkling Lights, an outdoor holiday light event covering six acres of outdoor gardens. As holiday music fills the air, visitors past trees lit with thousands of colored lights.

Portsmouth, New Hampshire

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7 Best New England Christmas Towns: Portsmouth, New Hampshire (Credit: Richard Cavalleri/Shutterstock)

Portsmouth’s vibrant working seaport celebrates Christmas all December long in true New England style. The Vintage Christmas in Portsmouth celebration includes outdoor ice skating and an annual Gingerbread House Contest delighting visitors each year. The event kicks off with a tree lighting in Market Square. Then enjoy a spectacular holiday parade featuring dancers, performers, marching bands and Santa himself.

Nantucket, Massachusetts

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7 Best New England Christmas Towns: Nantucket, Massachusetts (Credit: Shackleford Photography/Shutterstock)

Located 30 miles off the coast of Cape Cod, Nantucket is touted as the world’s whaling capital. Thousands of visitors are drawn to its quaint cobblestoned Main Street and iconic lighthouses. But the holiday season holds something special. Nantucket Noel kicks off the holiday festivities the day after Thanksgiving with an annual tree lighting ceremony. The celebration continues with Christmas Stroll Weekend beginning the next day. The events include live entertainment, a Village Marketplace and dozens of decorated Christmas Trees lining the streets. But the highlight is Santa’s arrival via Coast Guard Cutter to greet all who gather.

Woodstock, Vermont

Holiday
7 Best New England Christmas Towns: Woodstock, Vermont (Credit: James Kirkikis/Shutterstock)

Often hailed as one of the country’s prettiest small towns, Woodstock provides the perfect setting to celebrate the Christmas season. Each year, the second weekend in December sees Wassail Weekend festivities. Named for the ancient yuletide beverage made from hot mulled cider and spices, Wassail Weekend embodies old-fashioned New England charm. Activities include candle dipping lessons, holiday strolls and gingerbread ornament-making classes. There’s also a parade featuring decorated horse-drawn carriages ending with Santa arriving in his own wagon.

Stockbridge, Massachusetts

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7 Best New England Christmas Towns: Stockbridge, Massachusetts (Credit: James Kirkikis/Shutterstock)

If a holiday visit to this quintessential New England village leaves you feeling like you’ve just stepped into a Norman Rockwell painting, it’s with good reason. The artist’s 1967 work Stockbridge Main Street at Christmas became one of his most celebrated creations. Holiday events in Stockbridge take place the first weekend in December. They feature historic house tours, horse-drawn carriage rides and holiday concerts. But the signature event is the recreation of Norman Rockwell’s famous Main Street scene, complete with vintage automobiles parked along the street.

Mystic, Connecticut

Christmas
7 Best New England Christmas Towns: Mystic, Connecticut (Credit: Carol Ann Mossa/Shutterstock)

Along with its historic seaport and renowned aquarium, Mystic offers a special seasonal attraction. Mystic Seaport Christmas takes place the second week in December. Visitors line the docks in anticipation of Santa’s arrival by tugboat. They can also enjoy a tree lighting ceremony in Mystic River Park or a stroll through Olde Mistick Village’s street-lined luminaries. Or sneak in some last-minute Christmas boutique shopping.

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