With snow almost guaranteed in New England every winter, you are sure to find some of the prettiest winter towns around. These towns are noteworthy for their walkable downtown areas as well as attractions. Even if you aren’t the biggest winter weather fan, these towns will wow you with their charm.
OK, before you go farther I have 13 of the prettiest winter towns for you but let’s be real, you wouldn’t have clicked on this if the title was the 13 prettiest winter towns, right? I guess I could have included 2 more to give you 15 and maybe next year I will add 2 more. I hope you enjoy it.
Table of Contents
Maine’s Prettiest Winter Towns
Maine has so much to offer with each town you visit. Some of our favorite towns to visit are Kennebunkport, Camden, and Boothbay Harbor. These towns have wonderful festivals and events during the winter months to keep the visitors coming.
Yes, Kennebunkport is where the Bush family compound is. The Bush’s have vacationed in Kennebunkport for decades and have really added to the community.
This is one of the prettiest winter towns because they really do incorporate the sea into their winter theme decorations. I love seeing lobster traps made into a Christmas tree in the town square. I also love that people dress up as lobsters for the Christmas parade. This town certainly loves being on the sea.
Kennebunkport’s Christmas Prelude has all the activities and merriment that you need to start the holidays off right. This year most of the celebrations are online so be sure to check out all the events.
Don’t miss the Seashore Trolley Museum. Here you can take a ride on one of their restored early 20th-century streetcars into the woods. What a trip that is in the snow. In their museum, you can explore the history of the streetcar and also see their collection of restored trolleys.
Kennebunkport also decks their town out for Valentine’s Day. Every shop and building has hearts and specials for the day of love.
Camden is beautiful any time of year but during winter is sparkles. With its park and harbor, all lit up, a stroll along the boardwalk at the harbor is the perfect winter ending to a fabulous meal at one of the many great restaurants in town. However, if you are the adventure type, Camden has you covered too.
Camden Hills State Park has miles of hiking, ice climbing, snowshoeing, and cross-country skiing. If you’d like downhill skiing though head of to Camden’s Snow Bowl. This mountain is super special, it is the only place on the east coast where you can see the ocean while you are skiing.
However, you should not miss the premier event of the winter in Camden. The US National Toboggan Championship will be held on the first weekend in February 2021. Some of the teams even dress up in costumes so be sure not to miss this outstanding event if you are headed to Maine.
My family loves Boothbay. We especially love the botanical gardens. Their children’s garden area and woods are spectacular. Although they are closed in winter, they are open right now for Gardens Aglow. With thousands of lights, the gardens come alive and dance about for you. This is a drive-through event so be sure to attend and see the wonders of this garden.
Boothbay Harbor gets all decked out for the holidays as well. Capitalizing on their harbor, Boothbay’s festival of lights is centered around boats and everything to do with the sea. Even Santa and Mrs. Claus arrive by boat. However, the town shops and main street participate as well with lights and decorations for the season. Don’t be surprised if you see a Christmas tree made from lobster traps in several places in town.
If you like the Polar Express, then you shouldn’t miss out on taking a train ride at the Boothbay Railway Village. How spectacular is it to ride the train through town to meet Santa at the end? Hop off and see the village fully decorated for Christmas and get food treats at Harrington House Barn. This will make every child’s dream come true.
Of course, if you like to start the New Year off right, hit the ocean for the polar plunge. I love to watch as swimming run into the fridge cold water. The looks on their faces when they emerge are always a treat.
New Hampshire’s Prettiest Winter Towns
New Hampshire has two towns that make the list North Conway and Portsmouth. Both towns are worthy of a visit no matter the season but in winter they truly are picturesque.
North Conway is very well known for skiing, after all, there are five ski resorts within 45 mins of town. However, there are many activities to enjoy that have nothing to do with skiing.
For those who don’t ski you can go sledding, snowshoeing, ice skating, or even take a sleigh ride. Ice fishing, snow biking, cross-country skiing, snowmobiling, dog sledding, and even snowkiting are available in the area.
However, for me what makes this town one of the prettiest winter towns in New England is the shops along the main street. The shops really enjoy decorating in winter themes and invite visits to peruse their goods. This is one of my favorite things to do on vacation. I love to find new handmade gifts for my family.
If you visit in the month of December you can take part in all the Christmas and holiday festivals. The town gets decked out for the holidays and has train rides, Santa pictures, and more for you to enjoy.
If you are looking for outlet shops, North Conway has Settler’s Green. With 70 outlet stores to shop you are sure to find what you are looking for or forgot to bring from home. Nor will you go hungry while shopping since there are restaurants, cafe’s and even specialty shops like Lindt Chocolate Shop, Tails End Sweets & Treats, and White Mountain CupCakery.
Portsmouth, New Hampshire sits right on the coast and is everything one can ask for in a seaside city. From parks and museums to history and quaint shops, this town has a lot to offer. Even in winter, you should check out the city parks.
You can get some amazing views of Portsmouth by walking the Little Harbor Loop Trail or just by Wentwork-Coolidge Mansion. Also, Odiorne Point State Park is a beautiful spot to explore the coastline. You can also visit Seacoast Science in Rye.
The shopping in downtown Portsmouth on Market Street is quaint with local goods. Don’t miss G. Willikers! Toys & Books, your kids will love you for shopping here.
After dark head over to Strawberry Banke Museum has a wonderful holiday display throughout the month of December. You can also skate on Puddle Dock Pond at the museum. However, just walking around the grounds of this open-air museum you will enjoy the ambiance of the old houses and gardens.
One of the prettiest drives around Portsmouth is from the mainland onto Shapleigh Island to Goat Island to New Castle Island and back to the mainland. New Castle Island is so pretty with views for miles.
Vermont’s Prettiest Winter Towns
Vermont, like most of New England, has many smaller towns that could fit the criteria of prettiest winter towns but I’ve chosen three for you. For all the small-town charm and activities you can handle don’t miss Woodstock, Burlington, or Stowe.
Woodstock with its picturesque Woodstock Inn and covered bridge practically across the street just screams, prettiest winter town. Of course, both are always lit up to the nines for the holidays. One of the things I love most is walking the downtown area after dark to enjoy all the twinkling lights and decorations everywhere you look.
Skiing isn’t far from Woodstock with Suicide Six, Okemo, Pico, and Killington Mount Resorts within 1/2 hour. If it’s snowshoeing or cross-country skiing that you want, the Woodstock Inn offers those right our their back door.
I love that Woodstock has a town-wide “Deck The Door” contest. Residents decorate their front doors with festive merriment and then, this year, send a picture to be judged. I hope they put together a list of addresses for people to see all these wreaths and other decorations.
Woodstock also puts on a Wassail Festival. If you don’t know Wassail is a hot mulled cider. This drink is part of wassailing, which is a Medieval Christmastide English drinking ritual. This festival is supposed to bring a good cider apple harvest for the next year.
Billings Farm really gets into the holiday spirit with fun activities the whole month of December. You can snowshoe through the grounds or take a tractor ride around to see what the animals are doing. They also have candle dipping, ornament decorating, traditional fairy tale stories being told, and of course, hot wassail for all.
The shops of downtown Woodstock love this time of year when people come in from the color and explore their goods. You can easily get lost in the Yankee Bookshop but that’s not a bad thing at all. During wassailing, the stores also partake in a scavenger hunt.
Burlington’s Church Street is a wonderful pedestrian mall that you should take advantage of. This street is one of the reasons we think Burlington is one of the prettiest winter towns in Vermont. Even in summer, just strolling along Church Street is fun but in winter with all the twinkly lights and hopefully some snow it’s just magical.
The town of Burlington also has a holiday lights contest. They encourage everyone to decorate their house, condo, or apartment nearest to the street with a holiday display. There are three categories to enter, classic, colorful, and creative. But the best part about this contest is that you get points for being energy efficient. Love that the most.
In February, Burlington also puts on a winter festival for the kids. The activities range from face painting to dog sled rides to balloons to crafts and games. I love that there are indoor and outdoor activities at this festival. I hope they also have a snowman-making contest.
Burlington is really a town that loves winter. Their bike trails are maintained during winter months for biking and walking with the snow piled to one side for the snowshoers and cross-country skiers. Want to go sledding or ice skating well, the town has you covered there too. Enjoy Burlington has a full list of these activities and where you can participate in them.
Stowe has a great downtown area to peruse and shop. Lit up for the holiday’s Stowe makes you feel like you’ve escaped to the idyllic town away from the hustle and bustle of everyday life.
Not only does Stowe a picture-perfect walkable town but if you are a ‘foodie’ family like us, you will really enjoy Stowe. If you are in the mood for warm and cozy breakfasts try, Cold Hollow Cider Mill or seasonal farm-to-table meals try, Stowe Mountain Lodge. Of course, there are the local favorites of Hen of the Woods and in nearby Watertown, Ben & Jerry’s. This is their factory where you can also take a tour with tastings at the end.
One place you shouldn’t miss is the Trapp Family Lodge. Whether you only visit for a meal or take a maple sugar tour, or meet the cow you will love this lodge. And yes, this is the Von Trapp Family from the famous Sound of Music movie. Take the history tour and find out how the family ended up in Stowe, Vermont.
Massachusett’s Prettiest Winter Town’s
Since the 1950s when Norman Rockwell first painted his famous scenes from American life, we have pictured ourselves in those scenes. Well, the actual town that Rockwell painted in his Main Street at Christmas is on my list for the prettiest winter towns.
Stockbridge is the town depicted in Norman Rockwell’s iconic holiday paintings. The good old American 50’s Christmas scenes. Visit the museum to experience a miniature version of a winter scene of Stockbridge with trains. Be sure not to miss seeing the original paintings as well.
The Mount, which is Edith Wharton’s house, puts on great holiday and winter displays too. NightWood is a sound and light display they put on where you walk the grounds and enjoy the show. They also do a story walk for the younger set of visitors.
Naumkeag is another mansion in Stockbridge built during the Golden Age that puts on a light show. Enjoy their gardens lit up to sparkle during the holiday season.
The Berkshire area is also great for winter sports. You can enjoy skiing and tubing at Ski Butternut and enjoy tubing or go cross-country skiing at Hilltop Orchards. Hilltop Orchards also makes their own wine so check out their selection at Furnace Brook Winery.
Connecticut’s Prettiest Winter Towns
Maybe it’s because I love the movie “A Christmas in Connecticut” but I also think of Christmas here as a snowy scene with charming houses all decorated and people out caroling. Connecticut is quite charming and picturesque in a very New England way.
Did you know that Essex is one of the main towns Stars Hollow from Gilmore Girls, was based off? That idyllic small town old New England charm is what draws visitors to Essex every year. It’s fun just to walk the main street and take in a coffee but don’t miss the Griswold Inn. It’s one of the oldest continuously run inns in the states.
Make sure to see the festival “Candy Cane Lane” a Christmas and lights decorating contest for residents. After everyone has put up their lights the town will make a map for everyone to explore and discover all the festive displays. This is where you can see all the colonial architecture of the town.
Essex really gets into the season with their Holiday Stroll with horse-drawn sleigh rides with Santa, Storytime with Mrs. Claus, and caroling.
Don’t miss the Essex Steam Train & Riverboat’s “Reindeer on the Rails” excursion. This family-friendly train ride runs along the Connecticut River. The kids will receive reindeer antlers to wear along with a craft to do. The kids can also write Santa a letter for Rudolf to deliver. Certainly a train ride for everyone.
The Connecticut Train Museum is also putting on the 27th Annual Holiday Train Show until mid-February. This year there are new and larger exhibits with some hands-on toddler-size trains to explore. However, be sure to try your hand at the I-Spy game where you have to find objects in the displays. Certainly, a must-see event for all the train lovers in your family.
Mystic with its history steeped in the ocean has the charm of old-time England. The town shines anytime but is really special in the snow with all the lights glowing in the moonlight.
Mystic Seaport celebrates the holidays with its Lantern Light Festival. There is live music, a horse and carriage ride, a visit from St. Nicholas, crafts, games, and more. You can also see how the colonists prepare for the Christmas holiday and the new year.
Olde Mistick Village has transformed into a winter light spectacular. Lights are everywhere. The whole village is participating in decorating and adding lights to their stores, the walkways, and all the displays. What a great evening out even if it’s just to get some hot cocoa and see the lights.
To get some hiking and nature in head over to Denison Pequotsepos Nature Center. With indoor exhibits to explore and outdoor trails to hike this nature area along the Connecticut River is a gem and certainly a place to visit.
Loving these small town’s in New England? Well, then you should take this Coastal New England Road Trip.
Rhode Island’s Prettiest Winter Towns
The history and seafaring state of Rhode Island has so many places to explore that are just so picturesque in the winter. The coastline will give you great views of the water, harbors, bridge, and lighthouses but don’t miss these prettiest winter towns in Rhode Island.
Even though Providence is the capital of Rhode Island it has more of a small city feel. Explore the city parks especially Prospect Terrace where you will get a commanding view of the city skyline.
You should also explore Waterplace Park where the city holds the Waterfire Festival. The Waterfire festival is a magical festival of sculptures on fire on the rivers in Providence. It’s just spectacular.
The Roger Williams zoo has its drive-through Christmas lights spectacular that is a treat for everyone. Before seeing the lights check out the animals and the botanical gardens. The Roger Williams Botanical Gardens has the largest indoor greenhouse with gardens in New England.
If you’d like to see historic homes all decked out in lights head over to Benefit Street. Here you will see homes from the Gilded Age of glory. You can certainly get some inspiration for your own home decorations here.
If you are missing the traditional Nutcracker ballet this year then Festival Ballet Providence has you covered. This year they are putting on their version of “iconic Nutcracker moments” in a temporary outdoor venue for everyone to enjoy.
One of my all-time favorite things to do in winter is to ice skate outside. I truly think the experience is so much better outside. Well, Providence has you covered for a marvelous outdoor skating venue. BankNewport City Center is located right in front of City Hall. The setting couldn’t be better. Not only can you skate at BankNewport City Rink but you can also play on the ice in bumper cars. Yes, I said bumper cars on ice. Now that has to bring a smile to your face.
Going to Newport for a mansion tour during the holidays is quite spectacular. It should be on everyone’s list when visiting Newport, no matter what time of year you go. Take advantage of the setting and take your photos for holiday cards and to saver. The glitz and glamour of the Golden Age in America are on display for your enjoyment.
Another great idea for fun is to take the lighthouse cruise on the Coastal Queen. You will cruise Newport Harbor and Lower Narragansett Bay while seeing 4 lighthouses, mansions, the Pell Bridge, Fort Adams, and more. You can choose to be inside or out for this evening cruise that is sure to be wonderful.
Enjoy the view and ice skating at Gurney’s Newport Resort & Marina. If you go at dusk you will get a great sunset along with the Pell Bridge in the background. After you’re finished warm-up with your choice of hot chocolate flavors from the hot chocolate bar at the Chanler.
Pin for Later
Final Thoughts on the Prettiest Winter Towns in New England
I hope I have inspired you to get outside and enjoy these small towns all over New England. I know my family can’t wait to have the snow fly so we can have some winter fun in the snow and definitely stop for hot chocolate afterward. Have you been to any of these small towns? Which one is your winter favorite?