24 Magical New England Holiday Shopping Towns

Find unique gifts for everyone on your list at these merry New England holiday shopping towns.

By Bill Scheller

Nov 11 2022


Bowen’s Wharf in Newport, Rhode Island

Photo Credit : Erin McGinn

Your loved ones worked hard to earn their “nice” list status this year, so don’t entrust their perfect presents to warehouse elves and delivery-truck drivers. Make this the season you take back holiday shopping—back to the good old days when businesses were local, and magical retail displays buoyed the spirits of young and old. From big cities to small towns, New England’s merriest shopping destinations celebrate one-of-a-kind stores and boutiques; park-once, find-everything convenience; and sparkling seasonal events that make gift-hunting a joy.

Connecticut Holiday Shopping Towns

Guilford: Guilford’s town green is one of the loveliest in New England and may also be the most spacious: Each December, it welcomes thousands of locals and visitors to watch Guilford’s Christmas tree—not a cut import but a living evergreen—suddenly blaze with light. That night, several of the historic churches that face the green celebrate with events including a chili supper and holiday bazaar. Along Whitfield Street, boutiques Ella, Where She Shops, Flutterby, Tracy Brent Collection, and others draw shoppers, and the Spice and Tea Exchange lures gift givers wishing to stuff stockings with special fragrances. Over at the 1764 Thomas Griswold House, there’ll be cookies, cider, and caroling around the hearth.

Mystic: On land and on the water, Mystic shines throughout the Christmas season. Main Street, home of shops such as Bank Square Books and Manufaktura Polish Stoneware, is ablaze with light—but so are the vessels in the harbor, decked out for the annual lighted boat parade and the arrival of Santa by tug. At Mystic Seaport, Lantern Light Village and its walking tours are just that: lantern-lit, though with kerosene rather than whale oil. Olde Mistick Village, just north of town, is not about to be outdone, with a December and January Holiday Lights Spectacular welcoming shoppers here to browse Alice’s Haunted Little Bookshop, select Aran sweaters and Belleek china at Irish Eyes, and indulge that sweet tooth at Munson’s Chocolates.;

New London: The city on the Thames has a fun take on shopping local: Print your Holiday Passbook, spend at least $25 at participating merchants to get a stamp, and turn in 10 stamps to enter a drawing for a hotel stay and dinner. On Friday after Thanksgiving, follow the wreath-encircled antique streetlights to Parade Plaza, where the Christmas tree lighting raises the curtain on a month of “Merry Days and Jolly Nights.” Shop the Custom House Museum Shop for nautical-themed gifts, and visit Flavours of Life for fair-trade fashion and home accessories. Hungry shoppers head for the cozy, inexpensive Dutch Tavern, or for the great river views at On the Waterfront.

Ridgefield: Wearing its 300 years of history handsomely, Ridgefield’s Main Street turns Christmas-card-perfect with storefronts reflecting trees swathed in white firefly lights. On weekend evenings in early December, the Holiday Stroll brings locals and visitors together, with caroling, singing toy soldiers, and ice sculpting demonstrations. Downtown’s specialty retailers include must-stops such as Nancy O., with its luxurious yarns and accessories; the Toy Chest, stocked with distinctive playthings; and Audrey Road, the place for vintage-inspired clothing. Still browsing on Christmas Eve? Head for Books on the Common, open “till the last procrastinator leaves.” Refuel downtown, or catch one of the special Holiday Luncheons at the Keeler Tavern Museum, just south, where there’s also a Holiday Boutique on luncheon days.

Maine Holiday Shopping Towns

Boothbay/Boothbay Harbor: You’ll have a hard time finding anything that isn’t festooned with holiday lights in this seaside town, from Gardens Aglow at Coastal Maine Botanical Gardens to parades of lighted fire trucks and boats (one bringing Santa) on successive weekends after Thanksgiving. Downtown shops open for the Saturday-evening Early Bird Sale a week before Turkey Day, greeting shoppers who traditionally show up at places like Gimbel & Sons Country Store and Sherman’s Maine Coast Book Shop in pajamas and bathrobes. In mid-December, Men’s Night brings out the gents—in more subdued attire—for last-minute shopping.

Freeport: It’s New England’s only place to shop at any hour, 365 days a year—and to talk to a Christmas tree. The conifer at the corner of Main and Bow streets chats with passersby during Sparkle Celebration, which kicks off December 2 with a Parade of Lights and the arrival of Santa. But the real magic in this coastal town is its 170-plus factory outlets, an array of specialty shops, and the always-open L.L. Bean flagship store, where musical holiday light shows delight nightly. After stocking up on outdoor gear and saving a bundle at the outlets, pop into Wicked Whoopies to grab Maine’s official state treat, the whoopie pie, in both classic and gourmet flavors.

Kennebunkport: Kennebunkport goes out of its way to show it isn’t just a summer destination with its annual Christmas Prelude, a 12-day celebration (this year, Dec. 1–11) 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. The shoppers’ epicenter is Dock Square, where Daytrip Society offers unusual handmade clothing and housewares, and JAK Designs specializes in handmade knitwear and artisan jewelry. For nature-inspired holiday decor, head over to Snug Harbor Farm in adjacent Kennebunk—and don’t leave without sampling the buttery pastries at Boulangerie.

Portland:“Merry Madness” is the name of Portland’s Christmas game, and you’ll need to pick up a passport to participate (order online starting in late October). It’s a pocket-size booklet, good throughout December, that unlocks deals, discounts, and special offers at more than sixty city merchants. As you venture from shop to shop—perhaps taking in craft boutiques like Lisa-Marie’s Made in Maine, or Waterlily Handmade Gifts—the windows are as enticing as the wares, with some 40 shops and restaurants competing for a “best holiday display” award. All around downtown, Pandora’s Winter Lights brighten the nights (as will a stop for fries at Duckfat).

Massachusetts Holiday Shopping Towns

Great Barrington:This southern Berkshires town goes all out for Christmas on one big day—this year, December 10—with its Shop, Sip & Stroll celebration. There’ll be a hayride, games and crafts for kids, buskers, a youth choir concert, and the town tree lighting, followed by fireworks. On and around merrily lit Main Street, find unique shops such as Tom’s Toys, stocking everything from dolls to trucks to classic games; Karen Allen Fiber Arts, with carefully curated women’s designer apparel and other textiles; and Yellow House Books, specializing in used and rare volumes. Break for lunch at Marjoram & Roux—and after “Shop” and “Stroll,” the “Sip” part of the day might mean a visit to the handsome bar at Number Ten steakhouse.

Newburyport: Santa arrives at Newburyport Harbor on the Monday after Thanksgiving, courtesy of the U.S. Coast Guard, and hosts the tree lighting festivities in Market Square. On each of the following three Fridays, downtown merchants stay open late for Invitation Nights, and treat shoppers to light refreshments. The lights shine brightest on State Street, with shops such as Best of British and Green Thumb Vintage Goods—but don’t forget to stroll over to the boutiques in the nearby Tannery, perhaps pausing for fish and chips at State Street’s Port Tavern. Next stop: Custom House Maritime Museum, with its nautically themed holiday tree and gift shop.

Northampton: The holiday lighting might not be as over the top as in some towns, but Northampton’s compact Victorian center features an annual evening Holiday Stroll, plus galleries and boutiques that elevate gift giving to an art form. Whether the goods are quirky or classic, Main Street’s merchants make wandering its three long blocks a visual adventure. Handcrafted items—including many by New England makers—abound. Browse handmade jewelry, ceramics, kitchenware, and more at two downtown favorites, Kestrel and Pinch. To refuel, try artisanal baked goods, sandwiches, and the wintertime “Hot Bowl of Goodness” at Woodstar Café. And don’t miss Bag Day, a late November tradition in which thrifty shoppers save up to 20 percent at participating retailers.

Rockport: How else would Santa arrive in Rockport? He’ll come ashore via lobster boat on the first Saturday in December to preside at the Dock Square tree lighting. Later in the month, Rockport celebrates its 77th Nativity pageant and torchlit parade. As in the rest of the year, Christmas shopping in Rockport is all about Main Street and narrow Bearskin Neck, jutting to the Atlantic off Dock Square. The accent is on local craftsmanship at the Glass House (art glass and jewelry) and James Russell Goldsmiths, and on fun at Happy Whale Toys and Games and the venerable Tuck’s Candy Factory. And have a lobster roll at the Bearskin Neck Bistro … the lobster may have arrived with Santa.

New Hampshire Holiday Shopping Towns

Concord: New Hampshire’s capital launches the season with a gala Christmas Parade, featuring pipe-and-drum corps, clowns, antique vehicles, dancers, and, of course, Santa. Along Main Street, in the shadow of the State House, gift-hunting opportunities abound—look for Goldsmiths Gallery, home of custom jewelry designs; Fabulous Looks Boutique, for women’s fashions; Celeste Oliva, purveying extra-virgin olive oils and balsamic vinegars; and the flagship shop of the League of New Hampshire Craftsmen, where Granite State artisans display woodenware, blown glass, fabric creations, pottery, prints, and the league’s Christmas ornament, different each year. Craft beers are here, too, along with burgers and more at the Barley House.

Littleton:Cradled against the rushing Ammonoosuc River, Littleton welcomes the Christmas season with a Thanksgiving weekend parade highlighted by Santa’s arrival on a float pulled by massive draft horses. Holiday lights twinkle in the cupola of 1850 Thayers Inn, oldest hostelry in New Hampshire’s North Country, as shoppers stroll Main Street and browse Chutters, home of America’s longest candy counter; Little Village Toy and Book Shop; Just L, for midcentury modern antiques; and Lahout’s, for skiwear and winter apparel. Have breakfast at the Littleton Diner, then head over to the Rocks Christmas Tree Farm in nearby Bethlehem to cut your own tannenbaum. Back in Littleton, celebrate with one of Shilling Beer’s craft brews.

North Conway: North Conway’s Christmas-lit, mansard-roofed Victorian depot is the place to catch Conway Scenic Railroad’s Bartlett Holiday Special and Santa’s Holiday Express, for magical tours through the snowy countryside. Getting down to shopping business, head south of town to the outlets at Settler’s Green, which hosts its tree lighting on the first Saturday in December, and L.L. Bean’s factory store. In the village, the League of New Hampshire Craftsmen showcases Granite State artisanry, and at Zeb’s General Store, purveying only New England products, shoppers create their own gift baskets. Flatbread Company, at the historic Eastern Slope Inn, crafts pizzas using organic ingredients.

Portsmouth: Take a Christmas season walk through history with Strawbery Banke’s Candlelight Stroll, on the evenings of December 4, 11, and 18 (make sure to reserve your place early). Here in Portsmouth’s oldest quarter, you’ll meet costumed role-players, and wander streets lit by candles and bedecked with vintage decorations. Downtown Portsmouth lets electricity brighten the holiday display, and welcomes Santa with a parade and tree lighting on November 28. The red brick seaport hosts an eclectic array of shops, such as Riverrun Books (check out the vintage typewriters), Ireland on the Square, and the Portsmouth Candle Company.

Rhode Island Holiday Shopping Towns

Newport: Shoppers revisiting the Gilded Age in Newport will feel like hitting the shops with a pocketful of 20-dollar gold pieces. From late November through early January, three of the town’s famous “cottages”—The Breakers, The Elms, and Marble House—are bedecked in wreaths, evergreen swags, dozens of lavishly ornamented trees, and other period-appropriate decorations, while the Sparkling Lights display illuminates The Breakers’ grounds. Down by the waterfront, Newport’s compact colonial downtown harbors artisan galleries and boutiques such as Anchor Bend Glassworks, All Fired Up Pottery, and the myriad shops of Long Wharf Mall. On nearby Bowen’s Wharf, come in out of the chill for steak or seafood at Bowen’s Wine Bar and Grille.

Providence: Yes, Providence lights a Christmas tree—this year, on Saturday, December 3, in front of City Hall. The city also boasts a unique holiday spectacle: the display of floating torches called Waterfire, at sunset that same afternoon in Waterplace Park. From here, it’s a short walk to Providence Place Mall, right across from the gorgeously lit Rhode Island State House, where scores of national retailers have set up shop. Elsewhere downtown, the 1828 Arcade, America’s oldest indoor mall, hosts quirky shops including bookstore Lovecraft Arts & Sciences, honoring Providence’s master of weird fiction. Stick around the Arcade for a bite at Rogue Island Kitchen, or head up to Providence’s Federal Hill section and its renowned Italian restaurants.

Wickford: Santa shows up twice in Wickford: once at the tree lighting, which kicks off the town’s Festival of Lights on the first weekend in December, and again the next day when he arrives by boat. But he’s got nothing on his helpers, townspeople and visitors who show up that Saturday in their “elfiest attire” at Sweet Marie’s Tea Cottage for cocoa, cookies, and the start of the annual Elf Parade. Downtown, a short stroll along Main Street takes in shops such as Different Drummer, with a trove of handcrafts and local artwork; home goods purveyor Flatfish Cottage; and artisan boutique Serendipity.

Middlebury, Vermont
Photo Credit : Corey Hendrickson

Vermont Holiday Shopping Towns

Brattleboro: Sip hot cocoa as the tree is lit in downtown’s Pliny Park on the first Friday in December, then browse Brattleboro’s red brick downtown, where Vermont’s “shop local” spirit shines at shops like Boomerang, with its collection of throwback chic clothing; Altiplano, purveyor of Guatemalan-made jewelry; Vermont Artisan Designs, showcasing the work of Vermont craftspeople and fine artists; Turn It Up!, where CDs make room for vinyl; and three independent bookstores. Procrastinators aren’t forgotten here, with the Brattleboro Winter Farmers’ Market holding an annual Christmas Eve Market featuring handcrafted gifts and local specialty foods. Take a sushi break at Shin-La, or top off a successful day’s shopping with dinner at upscale Peter Havens.

Burlington: Pedestrian-only Church Street is where the holidays happen in Vermont’s pocket metropolis. On the day after Thanksgiving, caroling along Church Street Marketplace leads into the lighting of the city’s Christmas tree and a 100,000-bulb illumination along a four-block stretch that’s home to dozens of shops that include women’s apparel boutiques Dear Lucy and Whim, fine haberdasher Michael Kehoe, local crafts purveyor Frog Hollow, Crow Bookshop, eclectic housewares emporium Homeport, and stocked-to-the-ceiling Outdoor Gear Exchange. No shopper goes hungry or thirsty here, with perennial favorites Leunig’s bistro and Pascolo Ristorante, and Irish pub Ri-Ra, right on the Marketplace, and the Vermont Pub and Brewery one block away.

Manchester: Lots of towns have Christmas parades, but Manchester may have the only parade made up of tractors, each bejeweled with hundreds of lights. But while Santa rolls into town on a tractor, his helpers are already busy exploring southern Vermont’s biggest concentration of outlet shops, with names like Pendleton, Talbots, J.Crew, Michael Kors, and Armani; heading downtown to browse Northshire books, Vermont’s largest independent bookstore; or popping into The Italian Market for something Saint Nick might like better than cookies and milk. Just outside town, Robert Todd Lincoln’s Hildene is decorated for Christmas 1912, and the Wilburton Inn decks its halls in spectacular fashion.

Middlebury:You would actually have to live in this handsome college town to visit the entire cast of artisans, makers, and farmers packed into its 40 square miles; luckily, their crafts and wares are readily found throughout downtown. Middlebury Natural Foods Co-op is stocked with all things local, Vermont’s Own Products is the go-to for things like aged cheese and maple syrup (their fudge alone is worth the stop), and The Vermont Book Shop spotlights resident authors like Bill McKibben and Julia Alvarez on its packed shelves. For a little holiday sparkle, stop in at Middlebury-based Danforth Pewter, whose handcrafted creations include tree ornaments that are works of art. Meanwhile the annual December festival A Very Merry Middlebury offers specials, pop-ups, and promotions around town.

Woodstock: With its classic town green, three covered bridges, and walkable cluster of downtown shops and restaurants, Woodstock is a postcard-perfect Christmas season setting. The whole town is the venue for Wassail Weekend, December 9–12, with a parade, carriage rides, caroling, tree lighting, special events at Billings Farm, and a roaring Yule Log fire on the Green. Browse classic general store merchandise and souvenirs at the sprawling, 134-year-old landmark F.H. Gillingham & Sons; discover local artists at the Woodstock Gallery; and head over to the Woodstock Farmers’ Market for Vermont-made delicacies. Chilly? Warm up by the great hearth in the lobby of the Woodstock Inn.