Love Christmas in New England? From the historic charm of a quintessential Vermont village to the city glamour of a famed Rhode Island port, these 10 destinations are some of the best New England Christmas towns to visit during the yuletide season.
10 Best New England Christmas Towns
Portsmouth, New Hampshire
New Hampshire’s only coastal city celebrates the season with Vintage Christmas in Portsmouth, a monthlong celebration filled with “shows, strolls, and shopping.” Favorite activities include the Gingerbread House Contest, Candlelight Stroll at the Strawbery Banke Museum, and holiday shows at the Music Hall. Downtown, you’ll find plenty of boutique shopping and some of the state’s best dining.
Shop: Choose from a selection of trendy cards, gifts, prints, and premium wrapping paper at Gus & Ruby Letterpress; beautiful handmade gifts at Nahcotta; and everything the chef or baker in your life could ever want at LeRoux Kitchen.
Eat: Head to La Maison Navarre for French pastry staples such as macarons and crepes, or hit Row 34 for lobster rolls and oyster stew. Over at Moxy, which does New England cuisine with a tapas twist, try the “johnny cake community” (their take on cornmeal pancakes served with brown sugared pork shoulder) and whoopie pie sliders.
Courtesy of Freeport USA
Yankee once described this coastal town as “one of the great shopping destinations of New England, a small town where name-brand stores go for vacation.” It’s also a very merry destination when the holidays roll around. During Freeport’s annual Sparkle Celebration, signature events include the Sparkle Parade of Lights, the Sparkle Express on the Amtrak Downeaster, the Jingle Bell Run, concerts, the “Talking Tree,” and visits with Santa.
Shop: Browsing the L.L. Bean flagship store is a must (it’s open 24 hours a day, 365 days a year), and when you’re done stocking up on boots, gear, and rugged attire, more than 170 upscale outlets await.
Eat: Pop into Wicked Whoopies to grab Maine’s official state treat in both classic and gourmet flavors, or head to farm-to-table favorite Azure for an Italian-inspired lunch or dinner (try the Sicilian-style cioppino) paired with a Maine blueberry margarita.
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Courtesy of the Woodstock Chamber of Commerce
Tap into quintessential yuletide cheer in one of the state’s most picturesque villages. Enjoy ongoing holiday fun at Billings Farm & Museum or explore the town during Wassail Weekend, an event that includes historic home tours, a craft fair, breakfast with Santa, and a spectacular parade.
Shop: Browse classic general store merchandise and souvenirs to your heart’s content at F.H. Gillingham & Sons, stock up on cozy blankets at the Vermont Flannel Company, or select an heirloom-quality serving bowl or platter at Farmhouse Pottery.
Eat: Follow senior food editor Amy Traverso’s advice in her guide to Woodstock, and visit Worthy Kitchen for its craft beer and warming comfort food. She also recommends Mountain Creamery, “a great place to grab a VerMonte Cristo sandwich (ham, turkey, and Swiss between French toast slices, served with a side of maple syrup) and a slice of mile-high apple pie.”
Victorian street lamps lend an air of Dickensian charm to this coastal Massachusetts destination, where the holiday season kicks off with the Santa Parade and Tree Lighting in Market Square, followed by Christmas concerts and performances all December long. On Friday Invitation Nights, shops stay open late, plying visitors with refreshments, and the much-anticipated holiday house tour sponsored by the Custom House Maritime Museum offers a look at 10 festive historic homes.
Eat: Warm up with a tiki-inspired craft cocktail and cozy appetizers such as Maine crab rangoon and coconut curry mussels at the Paddle Inn, or satisfy your sweet tooth with bite-sized gourmet whoopie pies at Chococoa Baking Company.
Stockbridge Chamber of Commerce
Norman Rockwell made Stockbridge famous in his painting of the Berkshire town at Christmas, and the community pays tribute to that fact each year with Stockbridge Main Street at Christmas, a weekend celebration that includes holiday house tours, caroling, horse-drawn carriage rides, a visit with Santa, and a Sunday afternoon re-creation of Rockwell’s painting. Throughout the rest of the season, the Stockbridge region’s many cozy inns and award-winning dining options make it the perfect place for a holiday escape.
Shop: Pick up a book, ornament, or favorite print at the Norman Rockwell Museum, or head to the vintage-inspired One Mercantile in nearby Great Barrington for colorful kitchen enamelware, handmade wooden bowls, all-natural toiletries, and more.
Eat: Sip coffee and nibble croissants at No. Six Depot in nearby West Stockbridge, or choose one of the Red Lion Inn’s three on-site dining options for lunch or dinner: the elegant main dining room, the rustic tavern, and the cozy Lion’s Den pub.
The popular tourist town of Kennebunkport proves it’s more than just summer destination with its annual Christmas Prelude, a six-day celebration that includes a lobster trap Christmas tree, a pooch parade, multiple craft fairs, Christmas fireworks, and the chance to see Santa and his lobster elves arrive by lobster boat.
Shop: Located in the heart of Dock Square, Daytrip Society offers unusual and handmade gifts for everyone on your list. For nature-inspired holiday decor, Snug Harbor Farm in adjacent Kennebunk is one of the prettiest stops in southern Maine.
Eat: Test your limits for caffeine and buttery pastries at Boulangerie in Kennebunk, or treat yourself to a memorable “farm to fork” dinner at Earth at Hidden Pond, where the magical rustic ambience (a suspended apple tree serves as the dining room chandelier) is matched only by the just-caught, just-harvested menu.
Jackson, New Hampshire
Dreaming of a White Mountains Christmas getaway? With its small-town charm, classic covered bridge, and assortment of cozy inns, Jackson is the ideal anchor for a holiday escape. The town’s annual self-guided Inn-to-Inn Cookie Tour offers a peek inside nearly a dozen local inns, each serving at least one signature cookie.
Shop: In the heart of Jackson Village, stock up on White Mountain Puzzles to help make the long New England winter go faster. Just fifteen minutes away, bustling North Conway beckons with favorites such as Zeb’s General Store, the League of NH Craftsmen gallery, and dozens of national brand-name outlets.
Eat: Order a gourmet sandwich (we love the oven-roasted turkey chipotle club wrap) to go at J-Town Deli & Country Store, or sample artisanal cheeses and locavore creations like risotto served with locally foraged hen-of-the-woods mushrooms at Thompson House Eatery.
The Preservation Society of Newport County
Newport, Rhode Island
Gilded Age glamour meets Christmas coastal charm in this fabled Rhode Island port city. Christmas in Newport hosts citywide celebrations all December long, including concerts, craft fairs, and caroling, plus ongoing events such as holiday lantern walking tours. And running from mid-November through the new year, Christmas at the Newport Mansions includes seasonal decorations, Santa Sundays, and special performances of The Newport Nutcracker.
Shop: Head to retail hot spot Thames Street for distinctive finds at Thames Glass and Aardvark Antiques, or Bowen’s Wharf for American-made fashion and accessories at Kiel James Patrick and nautical-inspired totes at Sea Bags.
Eat: Enjoy all-day breakfast and BYOB Sunday brunch at Cru Café, head to Midtown Oyster Bar for Newport’s largest raw bar (featuring up to a dozen different kinds of oysters), or keep it simple with some of the best clam chowder in town at the Mooring.
Nestled along the banks of the Mystic River, the historic downtown of Mystic, Connecticut, is the perfect place to celebrate the holiday season. Don’t miss the lighted boat parade (including Santa’s arrival by tugboat) to kick off the season, and Mystic Seaport’s Lantern Light Tours, running weekends from Thanksgiving through Christmas.
Shop: Choose from hand-woven bracelets, doormats, and sailor knot ornaments at Mystic Knotwork; stock up on apparel and gifts at Tidal River Clothing Co.; or shop hundreds of fine spices, hand-mixed seasoning blends, and loose-leaf teas at the Spice & Tea Exchange.
Eat: Pair your coffee with a tempting spread of breakfast pastries and savory quiches at Sift, dig into gourmet burgers and craft beer at Engine Room, or earn your hardy-New-Englander cred with a winter cone of Mystic Turtle at Mystic Drawbridge Ice Cream.
Courtest of Edgartown Board of Trade/Joshua Robinson-White of Vineyard Lights Photography
The toniest town on Martha’s Vineyard, Edgartown is known for narrow streets lined with boutiques, grand 19th-century captains’ homes, cozy inns, and fine dining. But if you’ve visited only in summer, you’re missing out on one of New England’s most charming holiday traditions: Christmas in Edgartown, a weekend celebration that includes a Christmas parade, an arts and crafts festival, and the lighting of the Edgartown Lighthouse.
Shop: Browse two floors of reading material at Edgartown Books — perhaps with a coffee and pastry to follow at Behind the Bookstore, the café located (you guessed it) behind the shop. For a selection of fun accessories and colorful island-inspired jewelry, make tracks for Stefanie Wolf Designs.
Do you have a favorite New England Christmas town? Let us know in the comments below!
This post was first published in 2018 and has been updated.
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New England Holiday House Tours