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Best Christmas Celebrations in New England

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!

Santa arrives by boat at the Freeport Sparkle Festival.

Santa arrives by boat at the Freeport Sparkle Celebration in Freeport, Maine.

Courtesy of Freeport USA

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 2019***

Best Christmas Celebrations in New England

Wickford, Rhode Island | Festival of Lights
December 5 – 8, 2019

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!

freeport sparkle express

Freeport Sparkle Weekend in Freeport, Maine includes extra special rides on the Amtrak Downeaster.

Courtesy of Freeport USA

Freeport, Maine | Freeport Sparkle Weekend
December 6 – 15, 2019

This annual event in bustling Freeport (home to the L.L.Bean Freeport flagship store, several specialty shops, and a bevy of designer outlets) is a whirlwind of holiday cheer and excitement. Signature events include the Sparkle Parade of Lights, Sparkle Express on the Amtrak Downeaster, Jingle Bell Run, holiday carolers, concerts, and visits with Santa. Musical lights shows, horse drawn carriage rides, and the famous “Talking Tree” run all weekend long. Don’t miss posing with the giant L.L. Bean boot!

Norman Rockwell Christmas in Stockbridg

Celebrating a Norman Rockwell Christmas in Stockbridge, Massachusetts.

Stockbridge Chamber of Commerce

Stockbridge, Massachusetts | Main Street at Christmas
December 6 – 8, 2019

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 ChristmasStockbridge Main Street at Christmas

Kennebunkport Christmas Prelude

Kennebunkport Christmas Prelude

Robert Dennis

Kennebunkport, Maine | Kennebunkport Christmas Prelude
December 5 – 15, 2019

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 Tree in nearby Cape Porpoise!

SEE MORE: Kennebunkport Christmas Prelude | Photographs

Holiday Guide

Discover all the things that should be on your to-do list this holiday season in New England—when you download the FREE Yankee’s Ultimate Guide to the Holidays in New England right now!

nantucket stroll carolers

Nantucket’s Christmas Stroll

Nantucket Chamber Of Commerce/Michael Galvin

Nantucket, Massachusetts | Nantucket Noel and Christmas Stroll
December 6 – 8, 2019

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.–christmas-stroll

SEE MORE: Nantucket Holiday Stroll | PhotographsCome, Let’s Stroll | Christmas on Nantucket

strawbery banke candlelight stroll

Candlelight Stroll at Strawbery Banke in Portsmouth, NH

Strawbery Banke Museum

Portsmouth, New Hampshire | Strawbery Banke Candlelight Stroll
December  7, 8, 14, 15, 21 & 22, 2019

With a packed schedule of holiday fun, the historic seaport of Portsmouth, New Hampshire, is worth a visit all month long, 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

Woodstock Winter Wassail Weekend in Woodstock, Vermont.

Courtesy of the Woodstock Chamber of Commerce

Woodstock, Vermont | Winter Wassail Weekend
December 13 – 15, 2019

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

ogunquit christmas parade

Christmas by the Sea parade participants in Ogunquit, Maine

Nick Papin

Ogunquit, Maine | Christmas by the Sea
December 13 – 15, 2019

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.

Washington Valley Inn to Inn Cookie Tour

The Mount Washington Valley Inn to Inn Cookie Tour features treats like these from the Inn at Ellis River.

Elizabeth Campbell

White Mountains, New Hampshire | Inn to Inn Holiday Cookie Tour
December 14 – 15, 2019

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 christmas pops

Boston’s Quincy Market twinkles during the month of December.

Aimee Seavey

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.

Best Historic Christmas Celebrations in New England
Best Places to See Christmas Lights in New England
5 Best Holiday Light Displays in New England

The post Best Christmas Celebrations in New England appeared first on New England Today.

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