New England's Most Festive Towns for Christmas

The village of Jackson has been hosting a traditionally New England holiday festival for years. Think snow, sleigh bells, Santa, snow, covered bridges, Dickens readings and more snow. Jackson is located in the White Mountain area of New Hampshire. To enter the village you cross a covered bridge and find the winter wonderland. The festivities begin on 11/25 with open houses, storytelling crafts and cookie decorating. The festivities continue through three weekends. Check out the schedule of events on the website. If you are interested in the Jingle Bell Chocolate tour coming up you must call in advance. Seats on the sleigh sell out fast. Jackson is also located near North Conway New Hampshire where they have a famous Santa’s Express train ride.

Located in the Berkshire Mountains in western Massachusetts is the quaint village of Stockbridge. For 22 years the local Chamber of Commerce and residents have taken it upon themselves to make “Stockbridge Main Street at Christmas” one of Norman Rockwell’s holiday themed paintings come alive. The Norman Rockwell museum is also located in Stockbridge. This is a one weekend festival that runs December 3rd and 4th. The town is decorated in a Christmas theme complete with greens and lights. There are horse drawn rides, visits from Santa, story hour, holiday music and more. They even bring in vintage cars to replicate Rockwell’s painting. There are other activities in the area listed on their website.

Newport Rhode Island is known as a wealthy enclave, but not one that does not give back. During the holiday season this is especially true. Since the early 1970’s a local group of residents, business owners and community activists have been sponsoring Christmas in Newport. Their idea in 1970 was to provide non-profit holiday themed activities. That idea stands today. Amidst the scenic collaboratively decorated streets of Newport this non-profit organization raises funds for charity every year. During the holidays activities in Newport include productions of the Nutcracker and A Christmas Carol, movies, craft days, cookie decorating and tours of the famous fabulously decorated Newport mansions. There is also a Polar Express ride. Check the calendar for events held December 1st thru the 31st.

For the last 25 years Woodstock Vermont in central Vermont has hosted the Woodstock Winter Wassail Weekend in December. This year the event is December 9-11. This festival has a 19th century Vermont theme complete with carols, wassail, house tours, concerts, horses and wagon rides. The streets are festively decorated and stay open late for shoppers. Santa makes a visit and there is a kid’s theater production. The famous Vienna Boys Choir will also perform.

Kennebunkport Maine has a 25 year history of hosting the Christmas Prelude. Kennebunkport is an ocean front town so their celebration is decidedly nautical in nature. Santa even arrives by lobster boat. Other activities in the festively decorated town include a tree lighting, house tours, art shows, walking tours, chowder luncheons, fireworks, dancing and demonstrations. The festival is held December 1st-4th and 9th-11th.

Since 1981 the small town of Bethlehem Connecticut has been hosting a Christmas town festival. This town has a religious history with the first theological seminary in the US and the home of the Regina Laudis monastery. Their festival is free and is held on the town green. Kids can write a letter to Santa and have it postmarked with the famous Bethlehem postmark. They can also visit with Santa. There is a tree lighting, crafts, food, bake sales, concerts and choirs. The Festival is held December 2nd and 3rd.