11 Festive New England Towns To Visit This Holiday Season

When the holiday season arrives, New England transforms into a winter wonderland, offering a perfect blend of festive charm, cozy escapes, and outdoor adventures. Whether you’re drawn to the twinkling lights of quaint small towns, the charm of historic cities, or the serene beauty of snow-covered landscapes, New England in winter is nothing short of magical. Here are some towns I like to visit during the holiday season.

A large, illuminated pyramid-shaped holiday display with lights and ornaments in a town square at night. Buildings and bare trees are visible in the background. — Photo credit: Kailey MarcAurele.

Portsmouth, New Hampshire

A street intersection with a large Christmas tree, several brick buildings, and people walking. A Jeep is driving through the intersection. — Photo credit: Kailey MarcAurele.

Portsmouth, NH, is especially magical around the holidays, with its streets adorned with twinkling lights and festive decorations that create a warm, cozy atmosphere. The town’s charming holiday events, like the Christmas tree lighting, make it the perfect destination for anyone looking to experience a traditional New England Christmas.

Boothbay, Maine

Illuminated trees and a large face sculpture adorned with colorful lights reflect on the water surface at night, capturing the magic of New England holidays. — Photo credit: Kailey MarcAurele.

Boothbay, Maine is a great town to visit around the holidays. The town is decorated with lights and a buoy tree. The main attraction however is Gardens Aglow at the Coastal Maine Botanical Gardens. Be sure to get tickets in advance!

Mystic, Connecticut

A light display of a horse pulling a sleigh, made with colorful LED lights, is set against a dark night background in front of a building. — Image Credit: Image credit goes to.

There’s no shortage of things to see and do around Mystic during the holiday season. If you’re looking for free things to do, you can check out the festive decorations in Olde Mistick Village or in downtown Mystic. However, it’s also worth paying to experience the Mystic Seaport in during the holidays!

Newport, Rhode Island

Historic building lit with red and blue lights at night, surrounded by trees and holiday decorations. — Photo credit: Kailey MarcAurele.

Newport is a great festive destination to check out during the holidays with its historic mansions beautifully decorated for the season. Additionally, you can explore charming shops in the historic waterfront and festive events like the Christmas in Newport celebration or the lighting of Goat Island Lighthouse.

Provincetown, Massachusetts

Provincetown offers a unique and vibrant holiday experience, with its picturesque harbor town transformed by festive lights and seasonal cheer. The town’s art galleries and quirky shops create a welcoming atmosphere. They do a great job with making the downtown festive!

York Beach, Maine

Lighthouse and buildings on a rocky, snow-dusted cliff by the sea under a cloudy sky. — Photo credit: Kailey MarcAurele.

York Beach, Maine, during the holidays is a serene winter retreat, where the crisp ocean air and festive charm create a perfect seasonal escape. Nubble Lighthouse gets adorned with lights and wreaths, making it a must-see during the holiday season. York Beach offers a peaceful, scenic destination for those looking to unwind and enjoy a slower pace of holiday magic.

Bennington, Vermont

Red covered bridge over a snowy river, with a wreath above the entrance and clear blue sky in the background. — Photo credit: Kailey MarcAurele.

Bennington, VT, is a charming winter destination, with its quaint downtown adorned in festive lights and historic buildings creating a picture-perfect holiday setting. Visitors can enjoy a cozy stroll through the village, explore local shops for unique gifts, or warm up with a hot drink in one of its inviting cafes.

Deerfield, Massachusetts

A reindeer with a red scarf stands among snow-covered trees and festive lights. — Photo credit: Kailey MarcAurele.

The Yankee Candle Village in Deerfield, MA, is a winter wonderland, especially during the holiday season, with its massive candle store filled with festive scents and dazzling decorations. Visitors can enjoy the enchanting holiday displays, browse unique gifts, and watch skilled artisans create custom candles in the shop’s working candle-making area. It is a must-see for anyone looking to immerse themselves in holiday cheer.

stonington, Connecticut

A large pyramid-shaped structure made of decorated lobster traps glows festively against a sunset sky, making it a must-see among the festive things to do in Connecticut this holiday season. — Photo credit: Kailey MarcAurele.

Stonington, CT, is a picturesque coastal town that becomes even more charming during the holidays, with its historic village center lit up by twinkling lights and adorned with festive decorations. The annual Stonington Lobster Trap Tree is one of the best festive things to do in Connecticut during the holiday season.

Westerly, Rhode Island

Person standing under illuminated triangular arch in front of a building at night. — Photo credit: Kailey MarcAurele.

Westerly, RI, is a charming coastal town that comes alive with holiday spirit, from its twinkling lights to the festive events at local shops and restaurants. Be sure to check out the Starry Lights display in Wilcox Park in addition to the other festive lights displayed in downtown.

Essex, Connecticut

A park at dusk with Christmas lights decorating trees and a gazebo. A path leads through the scene with a lamppost illuminating the area. — Photo credit: Kailey MarcAurele.

Essex, CT, is a delightful New England town that exudes holiday charm, with its historic Main Street lined with festive lights, local boutiques, and cozy cafes. The town’s annual Trees in the Rigging Holiday Boat Parade, where brightly decorated vessels glide down the Connecticut River, adds a magical touch to the season, making Essex a great town to during the holidays.