Best Boston Holiday Events 2021: Markets, Music, and More!

Best Boston Holiday Events 2021 sowa

It’s the most wonderful time of the year to be in Boston. Grab your Purely Boston hoodie and check out the best Boston Holiday Events taking place in 2021. Whether you’re hunting for the perfect presents, looking to light a giant Menorah, or run through the streets in a Speedo, there’s plenty of holiday spirit in Boston.

SoWa Winter Festival

The 6th annual SoWa Winter Festival is running between December 3 – 12! With over 150 local art and food vendors, guests can enjoy indoor (mask required) and outdoor festivities such as food trucks, a beer garden, and design showrooms. View the schedule HERE. Address: 560 Harrison Avenue, Boston.

Winter Holiday Market at Snowport

Best Boston Holiday Events 2021 snowport

Head down to the Seaport and explore their Winter Holiday Market operating seven days a week through January 2, 2022. What better way to get your holiday shopping done while supporting locally-owned businesses? Address: 88 Seaport Boulevard, Boston.

Old South Church Christmas Craft Fair

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Mark your calendars because on December 4 the annual Christmas Craft Fair is taking place in Gordon Chapel. Stock up on soaps, jewelry, textiles, and other artisan products while enjoying live music provided by the Boston Conservatory Brass. Address: 645 Boylston Street, Boston.

CraftBoston Holiday Online

Get your holiday shopping done online this year. Shoppers seeking handmade, one-of-a-kind, and limited edition gifts should check out CraftBoston’s online showcase. 

Annual Kwanzaa Concert

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Roxbury Community College is hosting their Annual Kwanzaa Concert on December 18, 2021. Enjoy live performances from the Professional Dance Division and a candle lighting ceremony.  Address: 1234 Columbus Avenue, Roxbury Crossing.

Holiday Pops

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Arguably one of the best family-friendly holiday events in Boston, what would this list be without the Boston Pops? Check the calendar for a full schedule including Kids’ Matinees and sensory-friendly programs.

Light up the Night at The Chesnut Hill Square

Celebrate Chanukah at the Chabad at Chesnut Hill! The event takes place Sunday, December 5 starting at 3:30pm and features live music, Chanukah treats, and the lighting of a giant Menorah.

Chanukah Celebration at the Seaport

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Prefer to bring in the holidays by the water? Head to the Seaport Courtyard on Sunday, December 5 for family-friendly activities, live music, and more.

Santa Speedo Run

Keep an eye out between December 4 – 12 for Santas running around Boston in Speedos. The event began 21 years ago and has paved the way for the Play Ball Foundation! Participants are required to register in advance. 

A Christmas Story: The Musical

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Skip the 24-hour marathon of A Christmas Story and check out the musical instead! Ticket prices start at $25 per person and the event is taking place between December 10 – 19 at the Boch Center Wang Theater. Read more about the safety protocols here