10 Merriest Memory-Making Christmas Celebrations in New England


Traveling in 2021? Please check with each state/destination for its current COVID-19 guidelines, as these are constantly changing and the most accurate, up-to-date information may not be reflected here.

*Links in this article may be affiliate links, from which we may earn commission. See our Privacy Policy for full details.

There’s a brisk chill in the air and the world around you is blanketed in white; it’s Christmastime again! When the days grow shorter and darker and the nights grow longer and colder, something magical happens all across New England: towns and villages go all out to deck their halls (and Main Street) for the holidays, with cute, quaint, and simply spectacular Christmas celebrations that make the region all that is Merry & Bright! 

Whether you’re a life-long New Englander or simply a visitor in search of some holiday cheer, opportunity abounds for Christmas memory-making in the whimsical winter wonderland that is New England during the holiday season. Whether you’re looking for small-town charm or big-city bang for your buck, you’ll find it on this list of the 10 Merriest Memory-Making Christmas Celebrations in New England!

Christmas Prelude in Kennebunkport, ME

What better way to kick off the Christmas season than with a full week of fun festivities, a Christmas Prelude, if you will? Holiday activities for the week include gingerbread house making, Christmas carol sing-alongs, a Cookie Crawl, a “Pooch Parade,” and so much more! As much fun as Kennebunkport is year-round, at Christmas it transforms from a cute coastal town into a magical sea-side holiday port with festive wreaths, garlands, and twinkle lights everywhere you look.

In true Maine fashion, Santa arrives by lobster boat and yes, there is even a Christmas tree made out of lobster traps! The official tree lighting of the gorgeous (and massive!) evergreen is immediately followed by fireworks that light the sky behind it. If you’re not feeling the spirit of the season after a Christmas celebration like the Christmas Prelude, then you might be an actual, real-life Grinch!

Stockbridge Main Street at Christmas in Stockbridge, MA

Photo credit: James Kirkikis / Shutterstock.com

In a loving tribute to Norman Rockwell’s painting Home for Christmas (Stockbridge Main Street at Christmas),” the village of Stockbridge kicks off the holiday season with a weekend of Christmas festivities each year. Stockbridge Main Street at Christmas recreates the charm of the mid-century American Christmas experience; vintage cars line the street, carolers sing out from the wreath-decorated store-fronts, and celebrants enjoy horse-drawn carriage rides. Holiday stories are told and tours are given of historic properties, and yes, even Santa comes to enjoy the cozy charm of a Norman Rockwell Christmas. 

When looking for a Christmas celebration that embodies the quaint and cozy warmth of a small-town Christmas, it is hard to find any setting better suited for this task than Stockbridge, which was declared the “most charming small town in America” by global travel site Big 7 Travel. If you’re looking for vintage Christmas charm in your Christmas celebration, look no further than Stockbridge Main Street at Christmas!

Wassail Weekend in Woodstock, VT

Photo credit: James Kirkikis / Shutterstock.com

There are many festive ways to celebrate Christmas in Vermont, and Wassail Weekend in Woodstock is one that delivers big on both small-town charm and spirit of the season. Woodstock is a fun place to visit any time of the year, but Wassail Weekend sees residents and visitors alike gather together to make merry Christmas memories in what Conde Nast Traveler named one of the Most Beautiful Towns in America.

Tour some of the area’s most gorgeous historic homes and see how they deck the halls, stroll downtown amid the twinkle lights and fresh garlands and check out Woodstock’s unique shops (like local institution F.H. Gillingham and Sons), and catch a ride in a horse-drawn wagon, all the while enjoying the quintessential New England charm of this lovely Vermont village. A favorite event of the weekend is the Wassail Parade, where participants make their way around the town green, including Santa Claus himself!  After the parade, the yule log (more like a yule bonfire!) is lit and luminaries are placed all along the walkway in remembrance of those no longer with us. Wassail Weekend is without a doubt, one of the best Christmas celebrations in Vermont.

Vintage Christmas in Portsmouth, NH

Beautiful Portsmouth should be on the list of New England towns to visit no matter the season, but at Christmastime, this coastal town goes all out with their Vintage Christmas in Portsmouth, an entire month of festivities and Christmas celebrations. Entertainment includes musical performances, theater, and even comedy, a gingerbread house contest, a downtown scavenger hunt, and outdoor ice skating at lovely Puddle Dock Pond.

There’s plenty of shopping and delicious eats to check out, too, but a crowd favorite of Vintage Christmas in Portsmouth is The Candlelight Stroll, a whimsical tradition put on by Strawbery Banke Museum, where lighted candle lanterns and handmade wreaths adorn the walkways and role-players in period holiday dress mingle with guests. Vintage Christmas in Portsmouth attracts visitors from all across the region to celebrate Christmas, and it’s not hard to see why!

Newburyport Santa Parade and Tree Lighting in Newburyport, MA

The coastal village of Newburyport is picturesque and lovely at any time of the year (Maudslay State Park is an incredible leaf-peeping destination!), but come Christmas time, this quaint town has been referred to as “positively Dickensian!” Santa arrives via U.S. Coast Guard boat on the first Sunday after Thanksgiving and leads a festive Christmas parade through the square, but the first three Fridays in December are also full of holiday cheer with Newburyport Invitation Nights.

Newburyport Invitation Nights are the nights in which residents and visitors are invited to come downtown to enjoy live entertainment and complimentary holiday treats from local shopkeepers who are on hand to assist in the Christmas shopping process. Between the Santa Parade and the Newburyport Invitation Nights, there is no lack of holiday spirit and Christmas celebration in Newburyport!

Wickford Village Festival of Lights in North Kingstown, RI

Wickford Village is a spectacular example of quaint sea-side New England charm, and this village in North Kingstown opens its holiday season in early December with the Festival of Lights. Santa arrives by boat, led by his team of kayaking “reindeer,” and horse-drawn hayrides with Santa are a great favorite for “kids from one to ninety-two!” 

“Ye Olde Carolers” walk around the village, serenading attendees, and Christmas at the Castle is the cherry on top of the entire event with home-baked goods, mulled cider, cookie decorating, and children’s crafts. No one can make it through the Festival of Lights without feeling Merry & Bright!

The Annual Lighting of the Green and Christmas Parade in Taunton, MA

Nicknamed “The Christmas City,” Taunton, MA is well-known for how holly and jolly its Christmas celebrations can get! With a traditional Lighting of the Green and Christmas Parade that is over a hundred years in the making, The Christmas City knows how to host for the holidays! With live entertainment, family-friendly activities, and fireworks, there is plenty for all to enjoy.

All of the downtown shops and restaurants participate with holiday decorations of their own, but the most spectacular display is found on the actual city green. Surrounded by twinkling lights and beautifully lit displays, you will feel like you have stumbled upon a Christmas wonderland; with a nickname like The Christmas City, would you expect anything else?

Lighted Boat Parade in Mystic, CT

The beautiful waterfront town of Mystic is known for its rich nautical history, so it’s only natural that Santa himself should arrive in Mystic via tugboat on the Mystic River! One of many fun and festive events in Mystic for the season, Santa makes the rounds and visits with all who have come to greet him, and once it grows dark, the Christmas tree at Mystic River Park is officially lit.

The real fun comes just shortly afterward as the lighted boats arrive and begin their parade down the Mystic River. Revelers crowd around both sides of the waterway to watch the decorated boats travel down the river, their twinkle lights reflecting off of the surface of the water. Mystic’s holiday spirit doesn’t stop there, of course, as the Holiday Carnival takes place the following weekend with live music and festivities in Olde Mistick Village for anyone that just can’t seem to get enough of the Christmas fun that can be found in Mystic!

Christmas at the Newport Mansions in Newport, RI

Gilded Age mansions lavishly decorated with fresh and fragrant evergreen garlands, delicately hand-painted ornaments, and thousands upon thousands of sparkling lights? Yes please, sign me up for Christmas at the Newport Mansions! Newport is a beautiful coastal city and the mansions are certainly a pleasure to visit any time of the year, but it is during the holiday season that these jewels of Newport shine brightest. Where else on earth could you find a 15-foot “Poinsettia Tree?”

Tickets are available to tour the mansions and enjoy live music and refreshments, and of course, the Christmas celebrations do not end at the mansions! Newport also hosts other seasonal festivities like the Newport Harbor Illuminated Boat Parade and a Dickens Christmas Dinner Theater. If you are looking to sample a taste of the Gilded Age glory and luxury of Christmases past, then Christmas at the Newport Mansions is a must!

Sparkle Celebration in Freeport, ME

With a name like the Sparkle Celebration, is it any wonder that this Christmas event in Freeport is known as one of the most popular Christmas celebrations in all of Maine? With all the fun and frivolity that a name like the Sparkle Celebration implies, the event kicks off each year with a talking Christmas tree that comes to life on the first weekend of December! The “talking” Christmas tree loves to answer questions and participate in group sing-alongs, so come ready to interact!

Freeport dresses up to the nines with festive and fun holiday decorations and twinkle lights all throughout the town, and Sparkle the Stealth Elf makes her rounds to surprise lucky holiday shoppers with gift cards to Freeport shops! Nearby, the L.L. Bean campus hosts their Northern Lights celebration, a whimsical Christmas experience with daily musical holiday light shows, a twinkle light tunnel, festive and fun photo props, and more. With a name like Sparkle Celebration, how could it not help make your holidays merry and bright?

In New England, there are so many options for Christmas celebrations and holiday magic; whether you decide to head to the big city or visit one of the small towns that look like you’ve stepped right into a Christmas Hallmark movie, you’ll find some of the merriest memory-making Christmas celebrations in the country right here in New England. 


You might also like:


Leave a Comment

shares