The Most Magical Time of the Year – How to Spend the Holidays in Boston

holidays in boston Christmas Tree in Boston’s Faneuil Hall stands tall amongst the city’s buildings.

Twinkling lights, picturesque scenery, carolers …. And Santa in a Speedo? There is something for everyone to enjoy in Boston during the Holiday season. Plan to spend a day or even a weekend in our great city – you won’t be disappointed! 

Your Guide to Spending the Holidays in Boston


There are so many shows during the holiday season, there is no way to list them all. Here are a few that you may want to consider. Be sure to get your tickets soon because holiday shows tend to sell out quickly. 

You’ve heard of the Nutcracker but chances are Boston’s Sugar Plum Fairies are a little different than you’ve previously experienced. The traditional nutcracker, performed by the Boston Ballet, has showings in November and December. If you’d rather spend an evening watching a toy soldier infuse a little hop hop with Tchaikovsky, Boston has just the show for you! For a little diversity, the Urban Nutcracker adds a little jazz to the traditional dances by adding alternate dance styles like tap, flamenco, and more! 

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A Boston favorite, Holiday Pops, has multiple show options this season including a sensory-friendly show that is put together specifically with children or adults on the autism spectrum who may not enjoy the traditional show. There are also a couple of kids matinees so the younger set can join in the tradition with a shorter show to hold their attention. The kid’s matinees also include activities for the kids before, during, and after the show.  

Plan Your Visit! Explore Holiday Escapes >>

From Ariel’s undersea world to Arendelle with Elsa and Anna and to infinity and beyond with Buzz Lightyear, experience a magical holiday season with the whole family at Disney on Ice. There are only a handful of performances in Boston so you’ll want to secure your tickets quickly to this popular show. 

Music, unique instruments, singing, and dancing make the Christmas Celtic Sojourn a fascinating event. Clog your way down to the Cutler Majestic Theater to enjoy a performance. 

holidays in boston

Emerson Colonial Theater is offering Dolly Parton’s Smoky Mountain Christmas Carol featuring Ebeneezer Scrooge as the owner of a mining town. Featuring homestyle music, the show will be a heartwarming addition to your holiday season. 

RELATED: Lights, Camera, Action! This Fall, Boston Theater Aims to Delight


If you want to experience the Christmas season in Boston, there are plenty of options that won’t break the bank. If strategized well, you could fill a weekend with rich memories through free events. 

Boston BLINK Holiday Light & Sound Extravaganza in Faneuil Hall Marketplace is a must-see free event that features nightly performances every 30 minutes for the entire holiday season. 

Grab your skates and circle the rink a time or two at Boston Common. It’s okay if you have never skated before – chances are you won’t be the only newbie on the ice! 

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Mid-December, you are welcome to join the Boston Tea Party Reenactment. This yearly historical event may not be holiday related specifically but it’s definitely an event that your family will find educational and fun! 

If you find yourself in Boston during or right after a snowfall, don your boots and take an evening stroll through Back Bay and Beacon Hill. Featuring some of Boston’s most picturesque streets, you will feel as though you have stepped into Christmas Past. 


Take a break from the festivities and finish that shopping list. Faneuil Hall Marketplace has a wide array of “only in Boston” shops. You are sure to find something, especially for those who are a little trickier to buy for. 

shopping in boston

RELATED: Headed to Boston? Here are Four Favorite Shopping Destinations


Similar to trimming out the perfect gift, Copley Square Hotel has put together a fabulous holiday package that will make your holiday weekend in Boston complete. We know holidays can be expesive so we are offering a package that includes 25% off our elegant overnight accommodations, 25% off valet parking, and a morning continental bar to provide fuel for your day. We also offer our well-known Wine Down Hour for a perfect end to your magical day. 

Are you ready to book your trip? Full of good cheer, the staff at Copley Square Hotel is ready to help you create a wonder-filled holiday season. Give us a call! 

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