It’s truly hard to beat New England during the holidays! Between charming towns that transport you into a Hallmark movie set, heartwarming community events, appearances by Santa, tree lightings, and so much more, this region really knows how to celebrate the season.
This post is a guide on all my favorite Christmas festivals in New England to help you plan the perfect getaway! Over the years, I’ve experienced my fair share of Christmas festivities all over this area, and while every town does a great job celebrating the season, there are definitely a few stand outs that I’m excited to share with you today.
Whether you’re looking to spend a weekend in a quaint Christmas town, or are just visiting for the day, I’ll go over the events that are most worth your time. With that, let’s get started 😊
The Top Christmas Festivals In New England
1. Christmas Prelude In Kennebunkport, Maine
One of the most famous and iconic New England Christmas festivals is most definitely the Christmas Prelude event in Kennebunkport, Maine. This charming coastal town is worth a visit year-round, but during the holidays? Well, it transforms into one of the most magical places to be.
In fact, of all the Christmas destinations I’ve visited in the region, Kennebunkport definitely makes my top three.
The Prelude event pretty much has it all, and I always like to tell people that you probably can’t do and see everything in just one weekend. Between tree lightings, shopping events, fireworks, pop-up stores, festive decorations around town, hot cocoa bars, Santa’s arrival, and even a big Fire & Ice party, there’s so much festive cheer to go around. It’s no surprise that HGTV even named Kennebunkport the No. 2 Christmas town in the U.S.!
Prelude typically takes place the first two weeks in December, and to make sure all visitors have the same great experience, they even put on a tree lighting each Friday during the event to kick off that weekend’s festivities.
For Kennebunkport’s Prelude, I recommend visiting Thursday-Sunday, as that’s when you’ll have the most options for events around town. In fact, Fridays and Saturdays are the best days to visit.
Psst! I have a whole post on Christmas In Kennebunkport if you’re looking for more info, which includes tips for visiting 😉
Where To Stay In Kennebunkport At Christmas:
I highly recommend you book a hotel within walking distance to Dock Square, as parking downtown can be a bit challenging during Prelude. All of these suggestions are within walking distance!
🎄 Kennebunkport Captains Collection – A grouping of gorgeous historic homes, renovated into cozy inns.
2. Christmas Stroll On Nantucket, Massachusetts
Off the coast of Cape Cod in Massachusetts is the picturesque island of Nantucket, which is a popular summer destination in the region. But it’s also where you’ll find one of the most exciting Christmas festivals in the area!
The Nantucket Christmas Stroll typically takes place the first weekend in December, and is also packed with fun things to do, including Santa’s arrival by Coast Guard boat, stunning decorations around town, special shopping events, holidays markets, carol singers, and lots more.
But beyond that, the scenery of the island is simply picture-perfect at every turn this time of the year, and you’ll see historic houses decorated with wreaths and garlands, cobblestoned streets lined with trees, a giant wreath hung on Brant Point Lighthouse, and all the cheer from the local community is absolutely contagious. Be sure to also walk along Main Street after sunset, where you’ll find dozens of Christmas trees lining the street, which makes for such a special moment.
Psst! I have a whole post on the Nantucket Christmas Stroll, so be sure to check that out for more info 😉
Where To Stay On Nantucket At Christmas:
I recommend you stay at close to downtown Nantucket as possible during Stroll, as most events take place in that area, and parking is a challenge. These hotels are all walkable to the center of town!
3. Vintage Christmas In Portsmouth, New Hampshire
The charming city of Portsmouth along the coast of southern New Hampshire is another gorgeous destination to visit at Christmas. And their holiday event, A Vintage Christmas, is more than worth checking out.
During the Vintage Christmas celebration, visitors can attend a candlelight stroll through the historic houses at the Strawbery Banke Museum, which are perfectly decorated for the holidays. Step back in time while you’re guided by hundreds of glowing lanterns, and experience what it was like to celebrate Christmas in the 17th and 18th century.
Additionally, one of the most fun things to do during the event is go ice skating at Puddle Duck Pond at the museum, which is an idyllic outdoor rink backdropped by the beautiful, historic houses.
Be sure to also look for all the gorgeous gingerbread houses on display throughout town for the annual gingerbread house contest!
Portsmouth is also one of my favorite New England destinations for shopping, and all along market Square, you’ll find tons of boutiques with all kinds of unique gifts – all of which are tax-free in New Hampshire.
Where To Stay In Portsmouth At Christmas:
4. Wassail Weekend In Woodstock, Vermont
The most picturesque town in Vermont also just so happens to host one of the most fun Christmas events in New England – Wassail Weekend! Woodstock is one of the top places to go in the region if you’re looking for Gilmore Girls vibes, and the holidays here do not disappoint.
Wassail Weekend typically takes place the second weekend in December, making this one of the best times to visit Vermont during the holidays. It features a parade through town, horse-drawn carriage rides, craft fairs, ornament making, s’mores stations, and of course – wassail! This festive beverage is available in both alcoholic and non-alcoholic versions, and is served up on the town green during the event.
Additionally, Billings Farm and Museum in Woodstock also celebrates with their own events that correlate with Wassail Weekend for double the holiday cheer. Their Christmas at Billings Farm celebration takes place throughout December, and includes all kinds of fun things like candle dipping, mini pie making, horse drawn sleigh or carriage rides around the farm, marshmallow toasting outside for s’mores, hot cocoa, and visits with the adorable farm animals.
Where To Stay In Woodstock At Christmas:
5. A Traditional Christmas In Stowe, Vermont
Just over an hour from beautiful Woodstock is the adorable and quaint town of Stowe, Vermont. And their Traditional Christmas celebration is also one of my favorites.
Stowe is such a cozy little place with covered bridges, a lovely Main Street with great shops, wonderful hotels, amazing skiing – and well, the list goes on! But the Traditional Christmas celebration is the icing on the cake.
This festival typically takes place the first weekend in December, and it’ll be hard to not find your Christmas spirit while visiting. Featuring wagon rides around town, holiday markets, a tree lighting, appearances by Santa and Mrs. Claus, ice skating, a Santa Stroll shopping event, and lots more, it’ll be hard to do it all in just a day or weekend.
Where To Stay In Stowe At Christmas:
🎄 Trapp Family Lodge – Yep, that famous Trapp Family Lodge! 😉
6. Christmas In Newport In Rhode Island
Most famous for the stunning Gilded Age Mansions, you’ll find all kinds of amazing decorations, shopping, New England charm, and fun events while visiting Newport at Christmas. The first weekend in December kicks off Christmas in Newport with a magical tree lighting at Bowen’s Wharf, but really, the festivities take place all month long.
Throughout December, you can celebrate Christmas in Newport with special live performances, including The Nutcracker at Rosecliff Mansion, enjoy Sparkling Lights at The Breakers mansion, go ice skating with a view of Goat Island Lighthouse and the Newport Bridge, have breakfast with Santa, dine in an igloo, shop at all the incredible boutiques, and enjoy the gorgeous decorations all over town.
One of my personal favorite things to do in Newport during Christmas (besides the adorable ice skating rink and decorations!) is the Hot Chocolate bar at The Chanler at the Cliff Walk. Not only is the Cliff Walk an absolute must any time of the year in Newport, the Hot Chocolate bar is right at the start of the walk, and it’s the perfect way to get into the holiday spirit while enjoying some of the best views in the city!
Where To Stay In Newport At Christmas:
7. Snowport In Boston, Massachusetts
As New England’s largest city, you better believe that it goes all out for the holiday season! And the Snowport event in Boston’s Seaport district is one of the most fun to experience.
While Snowport is more like a giant holiday market destination than an actual festival, there’s so much more to do than shopping that I felt like it was more than worthy to be on this list.
In addition to the holiday market, which showcases over 100 vendors selling their beautiful creations, you can also attend the exciting tree lighting, admire the thousands of twinkle lights and decorations everywhere, dine inside an igloo, try your hand at curling, and generally, feel transported into a winter wonderland during your visit.
Where To Stay In Boston At Christmas:
8. Christmas By Candlelight At Old Sturbridge Village
Old Sturbridge Village is such a fantastic experience to have year-round, but it’s especially magical during their Christmas by Candlelight festivities in December. Step back in time to an authentic village from the early 1800s, and learn about holiday traditions, watch live baking demonstrations, listen to live music, shop for unique gifts from the Ox & Yoke Mercantile, and even meet Santa.
One of the best parts of this event, though, is the Christmas Tree Trail, which is why Old Sturbridge Village is also one of the best places to see Christmas lights in Massachusetts. Walk through a gorgeous display of lit trees that lead you to the charming Wish Bridge – and be sure to arrive at 4:30pm for the nightly lighting ceremony!
During your visit, plan the perfect night out by also stopping by the Ox & Yoke Café, which serves us delicious hot cocoa and homemade treats baked right inside the village. Then, spend the rest of your visit enjoying the decorations and exhibits inside each historic home and building.
Where To Stay In Sturbridge At Christmas:
9. Sparkle Celebration In Freeport, Maine
Just north of Portland is the wonderful town of Freeport, and their Sparkle Celebration is a Christmas festival you won’t want to miss if you’re in the area!
Typically taking place the first weekend in December, and continuing through the rest of the following week, this festival is packed with fun events like a very cool lights parade, tree lighting, the Sparkle Stroll and Frolic Festival, special shopping and dining events, and the beautiful Northern Lights at the Flagship L.L. Bean campus.
The festive Northern Lights event at L.L. Bean is one you’ll definitely want to have on your radar, especially since it’s right in the center of Freeport’s downtown. Running through the month of December, you’ll be able to walk through the twinkle light tunnel, take lots of festive photos by the giant snow globe, warm up by the fire pits with some hot cocoa, enjoy the awesome model train village that’s designed to replicate a charming New England landscape, and visit with Santa and his reindeer on the weekends.
Plus, you’ll want to be sure to head into the actual store to get some holiday shopping done, as L.L. Bean still makes some of my favorite things ever, and is on my list of the top places to shop for New England gifts!
Where To Stay In Freeport At Christmas:
10. Very Merry Middlebury In Vermont
Middlebury is a lovely college town in Vermont that celebrates the holidays with their Very Merry Middlebury event. Festivities take place every Saturday for most of December, and this is one you’ll want to swing by if you have a chance.
The first Saturday in December celebrates their exciting First Saturday Festivities, which is when you’ll get to meet Santa and Mrs. Claus, enjoy free wagon rides, pick up a cup of hot cocoa at the Hot Cocoa Hut, enjoy caroling, and participate in the chocolate bar raffle.
You’ll also want to plan to attend of the town’s Midd Night Strolls, which is a special shopping event around the charming downtown area with food trucks, promotions at the stores, and awesome pop-ups!
Where To Stay In Middlebury At Christmas:
🎄 Waybury Inn – The real life Stratford Inn from the beloved TV show, Newhart!
11. Main Street At Christmas In Stockbridge, Massachusetts
The famous Norman Rockwell painting Stockbridge Christmas on Main Street comes to life during this wonderful event in The Berkshires each year. Usually held the first weekend in December, the town pays homage to the cherished painting by recreating it along Main Street, which is still just as idyllic as the day it was painted in 1967!
Main Street is beautifully decorated for the festival, and during set hours, the town blocks off parking on Main Street and allows vintage trucks to park in front of the shops to replicate the painting – it’s truly such a unique and exciting thing to see.
Also during the festival, you can experience holiday concerts and sing-a-longs, historic home tours, Winterlights at the gorgeous Naumkeag estate, appearances from Santa, Victorian carolers, the Holiday Makers Market, and so much more.
Where To Stay In Stockbridge At Christmas:
🎄 The Red Lion Inn – Right on Main Street, so you’ll be steps from all the action.
12. Boothbay Lights In Maine
The quaint coastal town of Boothbay Harbor in Midcoast Maine celebrates the holidays with their Boothbay Lights festival, and this is one you don’t want to miss.
Events take place all December long, and it’s the perfect place to tap into your holiday cheer. First stop: snap a photo with the giant buoy tree, which will be the perfect souvenir to remember your experience by. Next, pay a visit to the Coastal Maine Botanical Gardens, which is transformed into a winter wonderland for their Gardens Aglow event.
And hopefully, you can time your visit just right and attend the Boothbay Lighted Boat Parade, which is followed by an awesome fireworks show, both of which typically take place the first Saturday in December. But before those evening events kick off, Santa arrives by boat earlier in the day, and there’s a very fun meet and greet with him for all the kids.
Can’t make it the first weekend in December? No worries! The festivities continue later in the month with the Gingerbread Spectacular. Visit the Opera House to see amazing gingerbread creations from the local community, and plan to stop by the Friends Booth to buy some homemade goodies to take home with you.
Where To Stay In Boothbay Harbor At Christmas:
13. Christmas In Jackson, New Hampshire
One of the absolute best towns in New Hampshire to visit during the holidays, and really, all winter long, is Jackson, which is nestled into the White Mountains. While Jackson doesn’t have a designated Christmas festival, it has so many amazing things to do during the holidays that I just had to include it on this list.
Nestlenook Farms should most definitely be on your itinerary for a Christmas visit. Their grounds are so magical at night when all the twinkle lights are turned on, and they offer lovely sleigh rides through their property.
The Chocolate Tour in Jackson is also one of the best ways to celebrate the season. This sleigh-led tour takes you to local businesses serving up chocolate creations for you to sample, without ever having to get out of the sleigh.
And lastly, you can stay at the most perfectly named hotel – the Christmas Farm Inn, which is located right in Jackson.
Where To Stay In Jackson At Christmas:
14. Christmas In Mystic, Connecticut
I mean, Hallmark made a movie for the 2023 season called Mystic Christmas, and it was actually filmed right in Mystic, so you know you’re in the right place to celebrate Christmas in Connecticut!
Fun Fact: My husband and I were in Mystic earlier this year while they were filming this movie, and we got to walk through the decorated set at Olde Mistik Village, which was so cool. We just watched the movie recently after it aired, and we loved it so much, and really appreciated that they filmed most of it right in Mystic. Anyhoo, moving on … 😂
Mystic is an adorable town along the Mystic River, and you’ll find so many festivities to celebrate the holiday season throughout December. Beginning with the Saturday after Thanksgiving, Santa arrives to Mystic by tugboat, and the tree lighting takes place later that day. Right after the tree lighting, enjoy the very cool lighted boat parade down the river! There are tons of places to watch the parade, too, making it a very enjoyable experience.
Throughout December, you can also enjoy lantern tours at the Mystic Seaport Museum, holiday decorations all over downtown, Northern Lights at the Aquarium, special holiday shopping events, the Holiday Carnival, and of course, the Downtown Holiday Stroll & Luminaria event, which is such a magical experience.
Where To Stay In Mystic At Christmas:
15. Christmas By The Sea In Chatham, Massachusetts
Last, but certainly not least, the Christmas by the Sea event in Chatham on Cape Cod is such a fun place to celebrate the holidays. Already a quintessential coastal New England town, the gorgeous decorations and festivities make this a top holiday destination, too.
The official Stroll event usually takes place the second weekend in December, and you’ll find horse and carriage rides, a tree lighting, light parade, and special shopping events along Main Street.
I also recommend that you visit the Chatham Bars Inn during a December visit (better yet, book a stay there if you’re coming in from out of town!). Not only do they offer you the option to have them decorate your room for Christmas before you arrive, they do tons of their own holidays events, too. Enjoy things like gingerbread house and wreath workshops, caroling and cocoa events, holiday mixology classes, holiday teddy bear tea parties for the kids, and so much more. Plus, the hotel’s decorations are simply dazzling.
Where To Stay In Chatham At Christmas:
🎄 Chatham Bars Inn – A Christmas destination all on its own!
1 Week Christmas Festival Itinerary For New England
If you’re planning a 7-day, or 1 week getaway in New England during the holiday season, I can help you decide where to go to maximize your time! Here’s what I suggest for a true road trip style trip through New England during the holdiays:
Day 1: Start in Boston for Snowport.
Day 2: Head to Cape Cod to spend 1 night, and either do the Nantucket Stroll as a day trip, or spend the day enjoying the festivities on the Cape.
Day 3: Drive to western Massachusetts and visit Old Sturbridge Village and Stockbridge (you can also just focus on one or the other for a more relaxed day).
Day 4: Head to Woodstock, VT for their festive holiday celebrations (even better if you can plan to arrive for their Wassail Weekend event).
Day 5: Drive to the White Mountains and spend a night in Jackson.
Day 6: Make your way over to Kennebunkport, Maine for the Prelude event (best to be there on a Thursday-Sunday).
Day 7: Drive back to Boston, stopping in Portsmouth, NH on your way.
If you’re looking for a more relaxed itinerary, here’s what I suggest:
Day 1: Start in Boston for Snowport.
Days 2-3: Head to Cape Cod to spend 2 nights, taking a day trip over to Nantucket for Stroll if you can time it right.
Days 4-5: Drive to Kennebunkport for 2 nights, stopping for a few hours in Portsmouth, NH.
Day 6: Drive to Woodstock, VT for 1 night (hopefully, you can time your visit with Wassail Weekend).
Day 7: Drive back to Boston, with an option stop in Stockbridge or Old Sturbridge Village.
What Kind Of Weather To Expect During Christmas In New England
Honestly, December weather in New England can vary quite a bit, and in recent years as temperatures have averaged higher than normal, I feel like it’s gotten harder to predict. It can also vary quite a bit depending on where in the region you are.
If you’re up in the White Mountains, northern Maine, or in northern Vermont, there’s a good chance for snow (but it’s not guaranteed just yet!). Along the coast of Massachusetts, including Cape Cod and Nantucket, it tends to be more mild and a bit warmer – you’re not likely to experience snow in December.
In places like Mystic, Connecticut, it also tends to be a bit warmer, and snow is usually unlikely.
In Western Massachusetts at places like Stockbridge and Sturbridge, it can be a bit colder, and there’s a good chance of snow, but it’s also not guaranteed here.
I always recommend that when you travel to New England any time of the year, you check the weather forecast a few days prior to your visit to get a better idea of what the weather will be like. Then, pack accordingly.
What To Pack For Christmas In New England
As mentioned, you’ll want to get a good idea of the forecast a few days prior, however, you can generally expect to pack these things for a December trip:
- A warm winter coat. A winter parka is better if you’re going to a snowy area, but a lighter wool coat will work for places that are typically a bit warmer. But remember, the nights will still be cool everywhere, so a warm coat is a must.
- Warm footwear. You may not need snow boots unless you’re planning to be in a snowy area, but you’ll still want to pack warm footwear. For more mild climates, I typically pack boots like the Sorel Out ‘N About ankle boots, which are waterproof in case of rain or slushy snow, but also work in light snowfall – or a clear day!
- Hats, gloves, and scarves – especially for the colder areas. These will also come in handy at night when the temperatures are cooler.
- Christmas sweaters, of course! The best way to stay comfortable in New England in the winter is by just wearing sweaters, and now is the time to proudly wear your favorite holiday sweater ☺️
- Dramamine if you get seasick, and are taking the ferry to Nantucket.
- Your camera, of course! You’ll get so many great photos during your trip.
- A reusable tote bag for holiday shopping, and reusable water bottle to stay hydrated.
More posts you may enjoy:
- Best Christmas Towns In New England
- Festive Things To Do In Vermont At Christmas
- Christmas In New Hampshire: All The Most Fun Things To Do
- How To Celebrate Christmas On Cape Cod
- Fun Things To Do In Newport, RI In The Winter (Including The Holidays)
That’s A Wrap On The Best Christmas Festivals In New England
And there you have it, the inside scoop on all the best Christmas festivals in New England. Whether you’re excited to take the ferry over to Nantucket island for their Stroll event, or if you can’t wait to get to Kennebunkport for Christmas Prelude, one thing’s for sure – it’s pretty much guaranteed you’ll find your Christmas spirit at every event on this list. Happy holidays!