Santa arrives by lobsterboat at the Kennebunkport Christmas Prelude
Photo Credit : Robert Dennis
It’s not hard to find the Christmas spirit in New England, but if you’re looking to visit a destination that guarantees a full dose of holiday cheer (we’re talking food, shopping, activities, and maybe even a glimpse of Santa), then these New England Christmas celebrations are the answer!
From candlelight strolls to Norman Rockwell charm, here are ten of the best Christmas celebrations in New England (listed by date in random order). Which would you most like to attend?
*** Updated for 2021***
Best Christmas Celebrations in New England
Festival of Lights | Wickford, Rhode Island
December 2 – 5, 2021
Historic Wickford Village in Wickford, Rhode Island celebrates the holiday season in seaside-style with a town tree lighting, hayrides with Santa, concerts, Elf Parade, breakfast with Santa, and more. Don’t miss Santa’s daily arrival at the Town Dock!
This annual event in bustling Freeport (home to the L.L.Bean Flagship Store, numerous boutiques, a bevy of designer outlets, and a hopping craft brewery scene) is a whirlwind of holiday cheer and excitement. Signature events include the Sparkle Parade of Lights, Talking Christmas Tree, Stealth Elf, Maine craft pop-ups, and visits with Santa. Enjoy ten full days of festive events, sales, and fundraisers among the dazzling light displays of their historic downtown Don’t miss posing with the giant L.L. Bean boot!
Celebrate Christmas in New England like Norman Rockwell! Rockwell made Stockbridge famous in his depiction of the town’s Main Street at Christmas, and the town pays tribute to the beloved painter each year in a weekend-long celebration of vintage holiday cheer. Holiday house tours, caroling, horse-drawn rides, a visit with Santa, and concerts make the weekend merry, but it’s tough to top the Sunday afternoon re-creation of Rockwell’s painting, complete with period automobiles.
SEE MORE:The Red Lion Inn in Stockbridge, MA | A Historic New England Inn at Christmas
The seaside village of Kennebunkport, Maine hosts a full week of holiday cheer each year with the Kennebunkport Christmas Prelude. Including the memorable arrival of Santa by lobster boat, events range from shopping and eating (take your pick from a pancake breakfast, lobster bake, or wine tasting) to special events like candlelight caroling, tree lighting ceremonies, arts & crafts shows, concerts, and much (much) more. Shops offer extended hours and many provide special treats to celebrate the season. Don’t miss the famous Lobster Trap Christmas Tree in nearby Cape Porpoise!
SEE MORE:Kennebunkport Christmas Prelude | Photographs
While picture-perfect holiday cheer abounds in Nantucket during the entire month of December, the island’s annual Christmas Stroll weekend is when the fun really begins. Starting with Santa’s arrival via Coast Guard vessel, the fun continues with craft shows, concerts, a holiday house tour, and Festival of Trees at the Nantucket Whaling Museum. Kid-friendly activities include visits with Santa and the Magical Talking Tree.
SEE MORE:Nantucket Holiday Stroll | Photographs, Come, Let’s Stroll | Christmas on Nantucket
With a packed schedule of holiday fun, the historic seaport of Portsmouth, New Hampshire, is worth a visit all month long as it celebrates Vintage Christmas, but we especially love the Candlelight Stroll at the Strawbery Banke Museum. Each weekend in December, the grounds are lit with the glow from hundreds of luminaries while the museum’s historic homes boast festive decor and all of the good sights and smells of the holiday season.
SEE MORE: Finding Christmas in Portsmouth, New Hampshire
Celebrating the holiday season in unique style, the annual Winter Wassail Weekend in Woodstock features a parade with over fifty horses and riders dressed in holiday costumes and period dress from the early 19th Century, concerts, a Saturday night Wassail Feast, historic house tours, yule log and activities for children. The shops in town stay open late for all of the names on your list.
SEE MORE: Wassail Weekend | Holiday Fun in Woodstock, Vermont
The popular Maine seaside town’s annual holiday celebration weekend features a tree lighting, Christmas parade, beach bonfire, polar plunge, fireworks, caroling, shopping, music, silent auction, living nativity, visits with Santa, the “Taste the Season” food festival, and more — much, much, more! You won’t know where to begin, but we promise you’ll have a holly jolly time.
If your idea of the perfect way to kick off the holiday season includes sweet treats, overflowing Christmas decorations, snow-capped mountain views, and the (optional but encouraged) cozy charm of a New England bed and breakfast, then the annual self-guided Mt. Washington Valley Inn to Inn Cookie Tour is exactly what you’re looking for!
See More:Mt. Washington Valley Inn to Inn Cookie Tour
Boston, Massachusetts | Christmas in the City
Whether it’s a day of holiday shopping on Boston’s city sidewalks, admiring the tree and musical light show at Faneuil Hall, treating yourself to a fancy dinner and performance of The Nutcracker or the Holiday Pops, skating on the Frog Pond, or even sipping a hot chocolate while cruising the city via trolley tour, Boston offers just about everything the urban holiday spirit desires. Bundle up and hit the town!
See More: Yankee‘s Boston Christmas Guide
Which New England Christmas celebrations are your favorite?
This post was first published in 2014 and has been updated.