New England has no shortage of towns that could be mistaken for a Currier & Ives print come to life, or, at the very least, the set of Gilmore Girls. All around the Northeast at Christmas, you can find plenty of cozy, light-strung streets to stroll, spiked cocoa in hand, but the largest density of holiday-ready villages is in Massachusetts.
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From communities with pristinely preserved historic districts and cobblestone streets to artsy towns with holiday light displays that rival the best in the world, Massachusetts is the destination for travelers who want to shop, dine, and explore in a landscape that feels like an enchanted snow globe.
Because you just never know what the winter will bring weather-wise, most towns in Massachusetts hold their holiday celebrations in early December. Even if you can’t be there for an official tree lighting or Christmas stroll, you can still soak in the festive atmosphere and visit the local attractions.
1. Andover
A handsome town nearly a straight 25-mile shot north of Boston, Andover is best known for Phillips Academy, the oldest and one of the most prestigious prep schools in the country. In 2018, gas fires damaged parts of the town, but it has since been quietly rebuilding.
For those who love big-city style without having to jockey for a parking spot, Andover is a great shopping alternative. Top boutiques include Native Sun, Savoire Faire Home, and Salt & Grove.
Head to the Addison Gallery at Phillips Academy to view an impressive collection of American art. Or enjoy the walking trails at Ward Reservation. At the top of Holt Hill, the highest spot in Essex County, snap photos of the “Solstice Stones,” a series of rocks arranged like a compass to mark the sunset on the year’s longest and shortest days. At night, Winterlights brings the Stevens-Coolidge House and Garden to bright, colorful life.
2. Concord
Concord, west of Boston, is where the “shot heard round the world,” which kicked off the American Revolution, was fired. To this day it has a different-drummer spirit.
Throughout the holiday season, the downtown, especially along Main Street, is beautifully decorated. A former literary hub — the likes of Nathaniel Hawthorne, Ralph Waldo Emerson, and Henry David Thoreau were visitors or residents — the town has a number of historic homes that also get in on the action. These include the Orchard House, which belonged to Louisa May Alcott, who wrote Little Women there. Sign up for a walking tour, or visit the excellent Concord Museum to view the exhibits.
If you’re traveling with grandkids, stop at the Toy Box, a combination toy store and arts and crafts shop with hundreds of Where’d you get that? products. Adults will enjoy the Cheese Shop, which has a much larger selection of international cheeses than you’d guess from looking at the small storefront.
3. Marblehead
A stroll around Marblehead feels so much like a trip back to the Revolutionary era, you might expect to see wool-waistcoated figures in tricorn hats gathering on every corner. This coastal town boasts about 300 densely packed historic homes, many of which are decked out in greenery swags, wreaths, and lights during the holidays.
Even if you can’t get there in time for the Christmas Walk (events December 1 through 4, 2022), you can still shop and dine around town. Have a cozy meal at 5 Corners Kitchen, and enjoy a nightcap at local favorite Maddie’s Sail Loft.
Hestia Creations on Hawkes Street sells adorable ornaments, nativity sets, and stocking stuffers. Grands will love their Sunday painting workshops, where they can practice their brushstrokes on a keepsake for Mom or Dad. Romantic Harbor Light Inn is a great choice if you plan to stay overnight.
4. Newburyport
Newburyport’s brick-and-cobblestone downtown makes a magical backdrop for a Christmas getaway. Walk between the Victorian streetlamps along avenues strung with lights, then pause in Market Square to admire the enormous tree, which practically drips with ornaments.
From late November through Christmas, you’ll find a comprehensive slate of holiday happenings. Grandkids will love Santa’s Workshop, across from City Hall, where they can peek through the window at Santa and Mrs. Claus and pen their own letter to Big Red. The town also hosts art shows, a makers market, chamber concerts, and a performance of Nutcrackah! a Bostonian twist on the classic ballet. Or explore the many shops, restaurants, bars, and more around this charming waterfront town.
5. Northampton
Northampton is a counterculture-cool city in western-central Massachusetts. Home to Smith College, it combines the exploratory spirit of academia with a stunning historic downtown and a vibrant alternative and LGBTQ scene. Northampton has a full holiday schedule this year, including gospel choirs, galas, and live music in a wide variety of genres and venues.
Check off your holiday gift list in the boutiques along Main Street, including Thornes Marketplace, a historic center filled with independent shops selling all manner of eye-popping goods. Warm up with a visit to Smith College’s Lyman Conservatory, a botanic garden whose greenhouses date back to the late 1800s.
Buck the holiday trend of ham and turkey dinners with a visit to one of the city’s best restaurants, Bombay Royale. Wrap up your visit with a stop at the Tunnel Bar, a former train-station pedestrian tunnel reimagined as an ambient cocktail lounge.
6. Oak Bluffs
Perhaps the most vibrant town on Martha’s Vineyard, Oak Bluffs is quintessential coastal New England. In non-snowy weather, plan to walk the North Bluff seawall, or visit one of the town’s three scenic beaches — even prettier in the hush of winter. Then visit the Gingerbread Cottages, a grouping of small, shingle-sided, brightly painted Victorian homes. It’s strictly a look-don’t-trespass opportunity, as the homes are privately owned. The historic neighborhoods along Seaview Avenue also make for a lovely walk. Or shop for gifts along Circuit Avenue.
Pro Tip: The Steamship Authority is the only ferry provider to Martha’s Vineyard in the winter. Service originates in Woods Hole and terminates on the island in Vineyard Haven. From there, it’s a 10-minute bus or taxi ride to Oak Bluffs.
7. Provincetown
Provincetown, or P-town to locals, is one of the most inclusive towns in Massachusetts. A longtime haven for the LGBTQ community, it’s welcoming to people of all ages, orientations, and backgrounds.
While cold temperatures and snowy streets will likely prevent you from partaking in the town’s exemplary beachcombing and biking, there’s still plenty to do at Christmas. The holiday season kicks off in early December with the cheeky Holly Folly and the lighting of the Lobster Pot Christmas Tree, a celebratory “evergreen” constructed from lobster traps and buoys. Throughout the month, you can also listen to live choral and pop music, take in a drag show, and admire the rugged beauty of the Race Point Light.
Christmas decor fans: Stop at Monty’s Christmas. Its collection includes Christopher Radko, Jim Shore, Old World ornaments, vintage music boxes, and more. Stay at the soothing White Porch Inn, a lovely boutique hotel that has its own integrated art gallery.
Editor’s Note: Headed to Provincetown? Don’t miss our picks for The Best Things To Do In Provincetown In The Winter.
8. Rockport
Like most coastal Massachusetts towns, Rockport is better known as a summer destination. But Christmas is a shining off-season moment, and not just because the whole town, including its lobster shacks, are gussied up in twinkle lights. This quirky little town pulls out all the stops for a full slate of holiday events, including Cape Ann Winter Lights, from late November through New Year’s Eve.
Depending on the day, you can take part in an Ugly Sweater Night, watch Santa arrive on a lobster boat or nativity figures parade up Main Street, or check out dozens of creative displays at shops that stay open till 8 p.m. Many local makers offer workshops, and kids can take part in a scavenger hunt that rewards them with sweet treats from Rockport confectioners.
Gift yourself a stay at the Emerson Inn. This boutique hotel, perched on a cliff above a wide-open bay that flows into the Atlantic Ocean, is a singular delight, especially in the off-season.
9. Shelburne Falls
Home to the famed Bridge of Flowers, which, in warm seasons, is decked out in colorful blooms, Shelburne Falls makes a sweet stop at Christmas. Although the bridge itself is closed in the winter, seemingly the entire town gets in on holiday decorating.
While in the village, look for the 12 tile murals that make up the Shelburne Falls Mosaic Murals Project. Each one teaches visitors about a different piece of regional history. The Shelburne Falls Trolley Museum is also worth a stop. Step aboard the old trolleys and pump cars, or channel your inner kid with the electric train sets in the visitors center. Have lunch at Baked, a snug restaurant and bakery that serves generous portions of comfort foods.
10. Stockbridge
Stockbridge is pretty much synonymous with Christmas, thanks to its most famous resident, Norman Rockwell. His 1967 painting Stockbridge Main Street at Christmas has been memorialized on everything from Christmas cards to coffee mugs. The artwork’s enduring popularity is celebrated each year in a real-life reenactment, with the historic charm of Main Street complemented by antique cars and shop decorations that evoke the 1950s.
Belly up to the bar at the Red Lion Inn for a hot seasonal beverage. Even better, pair it with baked goods from across-the-street neighbor The Lost Lamb, a patisserie that crafts exquisite croissants, cakes, and other treats.
At night, head over to Naumkeag, a Gilded Age “cottage” designed by lauded architects McKim, Mead & White. As darkness falls, Naumkeag’s expansive property sparkles with Winterlights, an 8-week celebration of illumination.
11. Sturbridge
Old Sturbridge Village, a recreated 1830s New England town, is the big draw of Sturbridge, near the border of Connecticut. Visitors flock to its Christmas by Candlelight celebration, which runs from late November through December. Besides holiday decorations throughout the 200-acre campus, the old-timey event includes a Christmas Tree Trail, Christmas Wish Bridge, demonstrations, live music and storytelling, snack samples, and a nightly lighting ceremony.
You can also shop for holiday gifts at the village’s mercantile, and vote for the Best in Show at the Gingerbread House Contest.
12. Williamstown
Home of the idyllic Williams College, Williamstown, in Western Massachusetts, doesn’t get the holiday attention of sister Berkshire towns like Lenox and Great Barrington. But whether or not you visit during its early-December Holiday Walk, its petite downtown, which has several restaurants and shops, is a year-round delight.
Williamstown is a top choice for art lovers. Between nationally renowned The Clark and the beautifully curated Williams College Museum of Art — not to mention modern art juggernaut MASS MoCA in neighboring North Adams — you could spend an entire weekend sampling a range of visual arts. Meanwhile, the ’62 Center for Theater and Dance hosts several winter performances, and Images Cinema shows first-run indie films all year long.
