Stockbridge, MA
The quaint town of Stockbridge isn’t only known for its stunning fall foliage, top-notch museums, and cozy bed and breakfasts, it’s also thought to be one of the prettiest winter towns in New England. Hop right into one of Norman Rockwell’s iconic American 50’s holiday paintings just by wandering the snow-sprinkled streets. Stop into Edith Warton’s house to view holiday and winter displays that are sure to get you into the jolly mood of the season. Staying in Massachusetts allows you to enjoy the winter festivities while also offering you the opportunity to ski, sled, skate, shop, and more in Stockbridge.
Kennebunkport, ME
Winter in Kennebunkport might as well be a vacation to the North Pole. Voted #2 best Christmas town in America by HGTV, this little fishing village in Maine goes all in on the holiday season. Watch Santa Claus arrive by lobster boat during the annual Christmas Prelude, attend the tree lighting ceremony in Dock Square, and join the chorus of Christmas candlelight carolers at the Franciscan Monastery. This town truly is a winter wonderland.
North Conway, NH
New Hampshire is home to some of the best skiing in the east, but the White Mountains offer way more to do than just hit the slopes for the day. Nestled at the base of the mountains, you’ll find North Conway’s main street, lined with shops and boutiques. During the winter months, these stores pull out their holiday decorations and transform the street into a village straight out of your favorite Christmas movie. Come for the decor and stay for the charming homemade merchandise that make perfect gifts for your family and friends.
Woodstock, VT
During the second weekend in December, this town in Vermont hosts Wassail Weekend, a three-day festival filled with twinkling lights, historic decorated homes, musical performances, ornament making classes, and holiday decorations at Billing Farm that harken back to historic 19th-century charm. Woodstock also has an annual town-wide “Deck the Door” contest, meaning that every house in the neighborhood typically is decorated to the nines. Grab a cup of wassail and join the festivities.
Essex, CT
Just like the movie, Christmas in Connecticut is picturesque in a way that screams old New England charm. They host an annual “Candy Cane Lane” festival that encourages residents to decorate their houses and stores with lights and holiday decor. Essex’s horse-drawn sleigh Holiday Stroll with caroling and storytime with Mrs. Claus is also a sight to experience.
Wickford, RI
This little town in Rhode Island is rich in history as it’s one of the oldest preserved Colonial villages in the country. Situated right on the water, the magic of Wickford comes alive when its old churches and historic homes are covered in a dusting of snow. You’ll find that you can’t help but imagine what life was like when this little village was first settled and built up. Stay in Newport, only a 20-minute drive away.
About New England Inns and Resorts
New England Inns and Resorts was founded in 1907 and has been devoted to providing unforgettable experiences ever since. With over 300 hotels, inns, and resorts located across New England, we support exceptional hospitality with a dedication to keeping it local at every location.
It’s true that seeing isn’t believing, but once you visit these towns you’ll find it hard to disagree: the best winter villages are in New England. After a chilly day of exploring, we know just the place to cozy up by the fire with a nightcap or cup of tea. Book your stay this winter.
