Sunday, June 14, 2026

festival locations to visit in new england during the holiday season


New England is as quintessentially a place to visit during the holidays as a Norman Rockwell painting. The weather is cool, the snow is falling and there is a festive spirit in the air. The New England vibe is a magical winter wonderland with all the warm, nostalgic holiday feel to it. Charming towns and cities in New England look like miniature resorts that come to life. There is so much to see and do in New England during this time, it can be hard to choose which ones to visit. From Christmas tree lighting and a visit from Santa in the Village Greens, to the annual Christmas celebration and Christmas decorations adorning streets, shops, restaurants and quaint bed and breakfasts, New England holidays are so unique and special.

If you’re looking for some fun trips to do in New England this holiday season, here’s a roundup of the best New England holiday spots sure to get you in the festive spirit.

festival locations to visit in new england during the holiday season

Woodstock, Vermont

Things to Do During Your Woodstock, Vermont Vacation

We may be biased, and honestly Woodstock, Vermont is our favorite place to go year-round – but especially during the holidays. Our town is brightly lit like a classic Hallmark movie. Often voted one of the best Christmas towns in America, the village’s trees twinkle with white Christmas lights, snow blankets the ground, and there’s true magic everywhere.This wonderland of winter holiday events begins with Thanksgiving, when our community comes together to celebrate the annual Zack’s Place Turkey Trotto raise money for our local Community Enrichment Center. Thanksgiving Weekend at Billings Farm Showcasing 19th century crafts, traditions and food for the whole family to enjoy!

Wasser weekend The annual Wassail Parade really rings in when the holiday season kicks off. The parade features over 50 horses, period costumes and festive costumes. During weekends you can enjoy holiday home tours, caroling and horse-drawn carriage rides. Be sure to take pictures under the middle covered bridge (opposite the Greenbelt Village), and in the distance you will see the bright stars at the top of Mount Tom.Don’t miss it when you’re in town Christmas at Billings Farm, Wassail Weekend at Billings Farm and BarnArts Holiday Cabaret: Let It Snow.

Where to Stay for a Woodstock, Vermont Vacation

Choose your accommodation from Woodstock’s charming B&Bs and inns. Some of our favorites include: Woodstock Inn, Jackson House, evening prayer, Blue Horse Inn and Woodstock Bed and Breakfast. Check woodstock guide Offers over 100 suggestions designed for mobile or desktop.

Newport, Rhode Island

Things to Do During Your Newport, Rhode Island Vacation

We all know Newport is one of our favorite Christmas towns. The Newport Coast is a scenic place where you can enjoy holiday festivities this season. Newport’s historic charm brings a lot to their holiday festivities. Walk the cobbled streets of twinkling lights, shops and restaurants filled with festive cheer. Newport hosts a range of events throughout the holiday season, including – Holidays at the Newport Building, Newport Parade of Lights, Bowen Pier Christmas Tree Lightingand Rosecliffe’s Newport Nutcracker. Check newport guide Hundreds of suggestions for what to see, do, eat and where to stay.

Where to Stay for a Newport, Rhode Island Vacation

There’s nothing like a Newport hotel dressed up for the holidays to get you into the festive spirit of the season.try Vanderbilt, Chanleror Castle Hill Inn.

Portsmouth, New Hampshire

Things to Do During Your Vacation in Portsmouth, NH

The beautiful coast is the perfect place to enjoy a vacation in Portsmouth, New Hampshire. A retro Christmas in Portsmouth feels warm, light and everything about a classic New England Christmas we know and love.The city lights up with stunning performances during the festival Music Hall Historic TheaterThis Annual Gingerbread House Contest and Exhibition, Outdoor Ice Skating and Strawbery Banke Museum and Illuminated Holiday Parade and Tree Lighting. We love everything about Portsmouth during our holidays!

Where to Stay for a Portsmouth, Rhode Island Vacation

Portsmouth Hotels Ideal place for your stay in the city.or try Wentworth by the Sea Marriott Hotel & Spa or Stage Neck Inn— Seaside boutique resort in York Harbor (20 minutes from Portsmouth).

Taunton, MA

Things to Do During Your Taunton, MA Vacation

For those looking for an urban festive atmosphere with a small-town feel, Taunton, Massachusetts in the Berkshires is the perfect getaway this holiday season.their famous Festival of Lights The light show at Taunton Green includes magical light displays, activities for the whole family and live performances. If you can’t catch the lights, you can enjoy the twinkling lights throughout the season and enjoy the outdoor activities of your choice in the mountains while you’re in town.

Where to Stay for a Taunton, MA Vacation

stay in The Colonel Brackington Get the feel of an intimate New England B&B just 20 minutes from town.

Boston, MA

Things to Do During Your Vacation in Boston, MA

Boston is such a fun city to visit during the holidays. It offers just enough festival-city festive cheer while also feeling manageable and not overdone.Ample opportunity to enjoy holiday activities such as ice skating boston frog pond, Holiday Theaters and Shows, Holiday Lights Trailstone zoo zoo lightsholiday pop, shopping and dining amid twinkling lights and cheerful city streets and more!

Where to Stay for a Boston, MA Vacation

try newbury boston or Whitney Hotel Enjoy an intimate boutique hotel experience in a big city.

Jackson, NH

Things to Do During Your Jackson, NH Vacation

Spend the Christmas season at the White Mountains in Jackson, New Hampshire.This Beautiful Christmas Town Has Its Own Character Christmas Farm Inn & Spago to Nestle Farm Toboggan, skate, and snowshoe, visit Jackson’s famous covered bridges, and take part in Annual Inn to Inn Cookie Tour and traditionally your celebration. Christmas in Jackson is charming and this season will fill you with warmth and light!

Where to Stay for a Jackson, NH Vacation

Stay in a Quaint B&B While Enjoying Your Vacation in Jackson – Try Briar Hill Inn or Christmas Farm Inn & Spa.

More of our favorite New England getaways

Freeport, Maine

Shine Celebration Lights Parade

Newburyport, Massachusetts

Santa Parade and Christmas Tree Lighting

Stockbridge, Massachusetts

christmas street

Kennebunkport, Maine

prelude to christmas

Mystic, Connecticut

festival of lights

Edgartown, Massachusetts

Christmas in Edgartown

Where do you like to go during your New England vacation? What are some of your favorite holiday events to enjoy in New England? Let us know in the comments below.

Disclosure: We may earn affiliate commissions if you purchase items through links on this blog. We only recommend products that we personally recommend. Thanks for your support.



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