New England

Best 5 Holiday Shopping Towns in New England

One-of-a-kind treasures and old-time Yuletide merriment bring the magic of the season to life at these 5 New England holiday shopping towns.

By Kim Knox Beckius

Oct 21 2016


Holiday shoppers stroll Congress Street in historic downtown Portsmouth, where shops such as the Portsmouth Candle Company provide inspiration for gift-giving.

Photo Credit : David J. Murray/Clear Eye Photo
Your loved ones worked hard to earn “nice” list status this year—so don’t entrust those perfect presents to warehouse elves and delivery-truck drivers. Make this the season you take back holiday shopping—back to the days when businesses were local and magical retail displays buoyed your spirits. New England’s merriest shopping destinations celebrate one-of-a-kind stores; park-once, find-everything convenience; and events that make gift-hunting a joy.
best holiday shopping towns in new england
Holiday shoppers stroll Congress Street in historic downtown Portsmouth, where shops such as the Portsmouth Candle Company provide inspiration for gift-giving.
Photo Credit : David J. Murray/Clear Eye Photo

Best 5 Holiday Shopping Towns in New England

Brattleboro, Vermont

In this throwback downtown set amid steep hills and wild rivers, historic brick façades showcase an extraordinary mix of old and new. Brattleboro is home to four independent bookstores. Find hot releases at Everyone’s Books, plus thrillers and crime at Mystery on Main Street; then peruse the trove of old volumes at Brattleboro Books and Basket’s. Within the city’s small footprint, you’ll find gifts from around the world—all with a local connection.

Don’t Miss:Holly Days, Holly Nights, when retailers and restaurants offer the season’s best deals. Must Shops:Boomerang (new and used vintage fashions), Gallery in the Woods (global and local handcrafts), Sam’s Outdoor Outfitters (sporting goods). Refuel:Deli-made sandwiches and hot selections at the Brattleboro Food Co-op.

LL Bean Freeport Boot
The famous Bean Boot at the L.L. Bean flagship store in Freeport, Maine.
Photo Credit : Aimee Seavey

Freeport, Maine

It’s New England’s only place to shop at any hour, 365 days a year—and to talk to a Christmas tree. What enables the conifer at the corner of Main and Bow streets to converse during Sparkle Weekend? Organizers will only reveal: It’s magic! Those two words sum up your search for cozy gifts, from flannel sheets to moose pajamas, in this coastal town’s factory outlets, specialty shops, and always-open L.L. Bean flagship store, where musical holiday light shows delight

Don’t Miss: Sparkle Celebration, featuring a parade of lights, train and horse-drawn wagon rides, and promotions. Must Shops:Wilbur’s Candy Shoppe (chocolate-factory tours and sweet gifts), Brown Goldsmiths (jewelry), Vineyard Vines Outlet (preppy attire). Refuel:Afternoon tea at the Harraseeket Inn.

SEE MORE:Visit L.L. Bean in Freeport, Maine | The Flagship Store

Northampton, Massachusetts

Don’t let Victorian-era architecture and subdued holiday lighting fool you: Cool downtown galleries and boutiques elevate gift-giving to an art form. Whether the goods are quirky or classic, Main Street’s surprising displays make wandering its three long blocks a visual adventure. Handcrafted items—including many by New England makers—abound, so when you spy the ideal gift, have it wrapped on the spot—you may never see anything like it again.

Don’t Miss:Bag Day, when thrifty shoppers flock to Thornes Marketplace first thing for shopping bags that entitle them to 20 percent savings at participating retailers. Must Shops: Kestrel (rustic home goods), Faces (novelties galore), PINCH (contemporary crafts). Refuel:Espresso and artisanal baked goods at Woodstar Café.

Portsmouth, New Hampshire

Step one: Board the free Vintage Christmas trolley on December weekends, and scope out the diverse shops along the brick sidewalks of this city by the sea. Step two: Resist the overwhelming urge to buy gifts for yourself. Actually, you’re already financially ahead when zero-sales-tax New Hampshire is your holiday-shopping headquarters, so treat yourself to a fun outfit or tickets to Disney’s Beauty and the Beast at The Music Hall.

Don’t Miss:Candlelight Stroll evenings at Strawbery Banke for Christmas and Hanukkah celebrations through the centuries. Must Shops:Pickwick’s Mercantile (Victorian-style wonders and small-batch perfumes), janegee (botanical bath-and-body products), Salt Cellar (gourmet seasonings and salt lamps). Refuel:Holiday Dinners at Strawbery Banke’s William Pitt Tavern.

best holiday shopping towns in new england
The 18th-century Keeler Tavern gives visitors a taste of colonial Ridgefield.
Photo Credit : Courtesy of Keeler Tavern Museum

Ridgefield, Connecticut

Holiday retail therapy meets 300 years of history along Main Street. Like a nostalgic Christmas card brought to life, gracious storefronts reflect red-beribboned lampposts and tree branches swarmed by white firefly lights. With tasteful gifts at down-to-earth prices and festive goings-on throughout December, don’t wait to visit—but come the darkening hours of Christmas Eve, Books on the Common is the one place, co-owner Ellen Burns assures us, “open until the last procrastinator leaves.”

Don’t Miss: Holiday Stroll, featuring free horse-drawn rides, shopping specials, and merriment. Must Shops:Nancy O. (luxurious yarns and “statement” accessories), The Toy Chest (distinctive playthings), Audrey Road (vintage-inspired clothing and gifts). Refuel: Holiday Luncheons at the Keeler Tavern Museum.