Wicked Holiday Guide

Wicked Holiday Guide

Christmas lights

Christmas is a magical time. Families travel far and wide to enjoy the holiday season by looking at Christmas lights, holiday displays and even travel to take pictures with Santa. There’s something about the holiday season that brings everyone together. And Massachusetts is home to two of the most magical Christmas towns in the country. Before we get to those, let’s take a look at what that entails.

The magazine Country Living did its rankings and from what they describe, it means “having fabulous light displays and shoppable Christmas markets full of fun holiday crafts to streets filled with I’ve-gotta-try-this-next-year outdoor Christmas decorations.” Two other towns in New England (but outside of Massachusetts) made the cut nationally. Essex, CT is known for a North Pole Express and Holiday Train Show. And Woodstock, VT is also listed. They mention cross country skiing and horse drawn sleigh rides as big draws for people wanting to get in the Christmas spirit.

When looking nationwide, Middleburg, VA is actually the #1 Christmas town in the country. They mention amazing holiday shops and shopping as well as a parade of hounds that takes place annually as just two of the reasons for its high ranking.

Now let’s take a look here in Massachusetts. There are several towns that rise above the rest and even two that are mentioned on top of the national list. We will explain why as we go but just know…taking a trip to either of these towns in the days leading up to Christmas will certainly get you in the Christmas spirit. If we miss one that you love, let us know.

  • Cape Cod, MA

    Okay, Cape Cod isn’t one town, it is listed nationally as one of the most magical places in America when it comes to Christmas. Reasons given are lighthouses covered in Christmas lights, craft fairs and parades.

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  • Stockbridge, MA

    Stockbridge is actually ranked #4 nationally because of the fact that it re-creates the 1967 Rockwell painting, “Stockbridge Main Street at Christmas.” They also have an annual festival that is coming up this weekend that celebrates the holiday like no other. 

  • Rockport, MA

    From its holiday shopping night, to its annual Christmas pageant, Rockport is loaded with things to do leading up to Christmas. Santa will even arrive in a lobster boat.

  • Edgartown, MA

    One of the main reasons Edgartown is mentioned is because of its Annual Christmas in Edgartown event. This year marks the 42nd annual and it’s coming up the weekend of December 7th. Here are what types of events you can look forward to:

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  • Nantucket

    Yes, Cape Cod islands can be festive too. From tree lightings to annual Christmas strolls to ugly sweater contests, Nantucket always is full of holiday cheer.

  • Taunton

    You may not think of Taunton when you think of Christmas, but anyone who lives there will beg to differ. The lighting of the green is one of the most spectacular events Taunton has to offer. The green itself is more than enough reason to visit this gorgeous display.

  • Concord

    There is a lot of charm and history in this small town. It is consistently voted one of the top towns to visit during the holiday season because of the lights and more specifically, the The Concord Festival of Trees. 

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  • Newburyport

    Lots of fun takes place annually in newburyport incuding Santa parade and tree lighting, singalongs, concerts, and holiday performances.  There is also a North Pole Express Train ride that is very popular. 

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