8 Best Places to Celebrate Christmas in New England

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There are many amazing destinations throughout New England to experience an especially magical Christmas. You’re likely to have at least a dusting of snow, and many of its historic towns look as if they’re a miniature-scale holiday village come to life. Most offer a wide range of festivities and often a host of outdoor adventures nearby like snowshoeing, cross-country or downhill skiing, sledding, tubing, and more. With so many great places, it can be hard to choose, but these are some of New England’s very best.

Taunton, Massachusetts
City of Taunton Lighting of the Green

Taunton, Massachusetts

The Berkshires offer a dream-like New England wintry holiday experience, with lots of charming small towns and classic red barns blanketed with glistening snow. Taunton is one of the best, with its Lighting of the Green and Lights on Festival taking place for more than a century. It may be the best small city Christmas lights and display presentation in all of southern New England, which is why it’s been called “The Christmas City” for so long. If you can be here in early December, you can enjoy the opening night festivities and fireworks, but the magical holiday scenes can be enjoyed throughout the month. Nearby, enjoy cross-country skiing or snowshoeing over mountain trails as you explore the landscape that looks like a Norman Rockwell painting.

Woodstock, Vermont
Christmas lights in Woodstock, Vermont

Woodstock, Vermont

The historic town of Woodstock offers that quintessential, idyllic Vermont Christmas, with the ground almost always covered with at least a light dusting of snow and the scent of pine needles waft through the air. One of the best Christmas towns in the world, the magical city hosts Wassail Weekend, a pre-holiday festival with 19th-century Norse culture tradition that includes a parade with over 50 horses and riders that don holiday costumes and period dress, along with wagons, sleigh rides and a Christmas celebration at the Billings Farm & Museum. There are many lovely inns and B&Bs in the area, perfectly situated for easy access to the Killington and Okemo ski areas, like Jackson House Inn as well.

Kennebunkport, Maine
Kennebunkport Annual Christmas Prelude

Kennebunkport, Maine

Kennebunkport is one of the best stops on Maine’s scenic coast, offering the chance to walk deserted beaches along wild shores that are even more photogenic when shrouded in snow. In Kennebunkport, you can watch Santa Claus arrive by lobster boat during the annual Christmas Prelude during the first half of December, and plenty of other festivities throughout the holiday season, like a seashore trolley holiday ride, wine tasting, and lobster bakes. For an especially romantic Christmas state at one of the area’s inns, like the White Barn Inn with its Arts & Crafts-style Wharf Cottages that include flagstone fireplaces.

Middlebury, Vermont
Middlebury, Vermont

Middlebury, Vermont

The historic village of Middlebury dates back to 1761 and is magical at Christmas, tucked alongside Otter Creek in the hills of western Vermont. Enjoy month-long holiday cheer that includes a whimsical hut serving hot cocoa on the town green, starting with the arrival of Santa in early December. All sorts of activities in the snow can be enjoyed nearby, including skiing and boarding as well as sledding, snowshoeing, sleigh rides and even dog sledding. After a day of play, you’ll find inns and hotels that offer full-service spas for pampering too.

Stockbridge, Massachusetts
Red Lion Inn in Stockbridge, Massachusetts

Stockbridge, Massachusetts

This town made famous by Norman Rockwell’s painting of the village during the holidays is truly magical with its New England setting decorated in festive lights, wreaths and holiday decor. Early in December is a celebration in Stockbridge that includes holiday house tours, caroling, and a holiday concert, but all month long you’ll find something to enjoy like the WinterLights at Naumkeag, a National Historic Landmark and gilded age mansion illuminated with thousands of shimmering holiday lights and designed light installations. Every weekend there are performances and activities, including live music, children’s activities and more.

Portsmouth, New Hampshire
Portsmouth, New Hampshire

Portsmouth, New Hampshire

Vintage Christmas in Portsmouth is a month-long celebration with shows, dazzling lights, shopping and much more. Catch a holiday show at the Music Hall Historic Theater,  celebrate the official kick-off of Vintage Christmas cheer at the Annual Gingerbread House Contest Exhibition that features elaborate gingerbread houses nestled into a winter wonderland gallery, enjoy outdoor ice skating every day in December and the countdown to the lighting of the Portsmouth Christmas three. The holiday fun continues with an impressive illuminated holiday parade down Islington Street and through Market Square.

Jackson, New Hampshire
Jackson, New Hampshire

Jackson, New Hampshire

Crossing the covered bridge into Jackson is like stepping into an entirely different era. Discover a place where tranquility and picturesque scenery merge to create the ultimate escape from the chaos of the modern world all year round, but perhaps even more so in the winter. Its circular green circled by inns, antique shops, and cafés has made it a favorite yet well-hidden resort town since the mid-19th century. There’s no commercialism here though you will enjoy easy access to the Presidential Range and Mount Washington and the Presidential Range, a panorama of peaks that can be seen from downtown. There are miles and miles for trails that lead cross-country skiers alongside a creek or high up into the mountains, while downhill skiers visit Black Mountain, the oldest lift-served ski area in the state known for its breathtaking vistas. 

Rangeley, Maine
Cupsuptic Lake, Rangeley, Maine

Rangeley, Maine

If you want to be surrounded by a vast snowy wilderness while hunkering down in a cozy inn, it’s hard to beat Rangeley, a winter wonderland dotted with spruces and pines that are heaving with snow and dotted, while lakes are frozen over underneath the white blanket of nature. It’s a playground for snowmobiling, snowshoeing and ice-fishing, while skiers can head to nearby Saddleback on the northwestern slopes of Saddleback Mountain. The town itself offers lots to do like holiday concerts, the annual parade of trees and all sorts of events that include shopping and dining specials, refreshments, horse-drawn wagon rides, family activities, tasting events and contests.

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