8 Christmas Towns In Massachusetts That Will Fill Your Heart With Holiday Cheer

The quaint Berkshire town of Stockbridge is the quintessential spot to celebrate the New England holiday season. Not only is this small town known as the Christmas Capital of Massachusetts, it has also been repeatedly ranked as one of the most festive holiday spots in the country. The town comes alive with holiday cheer as it pays tribute to its most famous citizen, artist Norman Rockwell, and his beautiful painting named "Stockbridge Main Street at Christmas." Festivities include historical tours, live performances, a holiday market, and a reenactment of Rockwell’s holiday painting. The Norman Rockwell Museum will also host special holiday exhibits including opportunities to view Rockwell’s famous Christmas painting.

Celebrate Christmas by the sea in the coastal town of Rockport, where Santa often arrives in town via a lobster boat! The whole month of December will be filled with festive family-friendly activities including a holiday farmer’s market, tree-lighting, Christmas singalong, and holiday shopping stroll. The town’s annual Christmas pageant is also an event that should not be missed. Now in its 78th year, this live re-enactment of the nativity is a beautiful town tradition.

Martha’s Vineyard may be most heavily visited in the summer, but there is also lots of Christmas fun to be found on the island. Head to charming Edgartown and celebrate the season with a holiday parade, festive road race, horse-drawn carriage rides, and a winter market. The annual lighting of the town’s historic Edgartown Lighthouse is always a magical experience.

And there is more Christmas cheer taking place on the island of Nantucket. The seasonal celebration kicks off in late November with the lighting of the island’s Christmas tree. Nantucket’s annual Christmas Stroll follows during the first weekend in December. This time-honored holiday event features a festive European-style marketplace, Victorian carolers, a visit from Santa via a Coast Guard cutter, and a hilarious ugly sweater contest. There will also be an opportunity to hit the ice and skate with Santa at the Nantucket Ice Community Rink.

The city of Taunton, Massachusetts is fondly nicknamed "The Christmas City" for good reason. Taunton has some of the best Christmas events in Massachusetts. Throughout December, this festive spot comes alive with parades, live readings of "A Christmas Carol," and Taunton's spectacular annual holiday light drive-through light festival. This is one show that you won’t want to miss!

If you are looking for some quaint New England charm, Concord is one of the best places to visit at Christmastime. This historic area transforms into a winter wonderland during the holiday season as locals and visitors enjoy a shopping stroll through West Concord, a Holiday Pops concert, and the town’s beloved Family Tree tradition featuring over 30 decorated trees and wreaths inspired by favorite works of literature. And speaking of literature, Concord’s historic Louisa May Alcott’s Orchard House will also be hosting an old-fashioned Christmas celebration where guests can enjoy period music, games, and decorations.

Newburyport is one of my favorite places to visit in Massachusetts. It is particularly wondrous during Christmastime when the cobblestone streets are filled with shoppers and the city is decorated in festive colors. Along with some great holiday shopping events, Newburyport also hosts a Santa parade and tree lighting, singalongs, concerts, and holiday performances. A popular family event is the North Pole Express Train ride which departs from the Newburyport Commuter Rail Station.

There is nothing more magical than spending Christmas in the city, so although it’s not a town, I just couldn’t leave Boston off this list. From the annual Christmas tree lighting on the Boston Common to Nutcracker Performances and Holiday Pops concerts, there is so much fun to experience in the city this year. You can even enjoy some holiday cheer out on the water by taking a cozy hot chocolate cruise around the harbor.