Your Downtown Springfield Holiday Bucket List

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If you find yourself in Downtown Springfield during the most wonderful time of the year, you might be asking yourself, “What can I do to have the hap-hap-happiest time of my life?”

Well, since you asked, here are A LOT of things to do around the holidays in downtown …






Stop at the William C. Sullivan Regional Visitor Center this holiday season. You can find everything from FREE passes to the Springfield Boys and Girls Clubs Festival of Trees to discounted Bright Nights tickets and more. Enjoy the new “Outside the Box” Gift Shop with special local made gifts.



December 29 – December 15 | MassMutual Center

We invite you to celebrate the holidays at the Springfield Boys & Girls Club’s 19th Annual Festival of Trees located in downtown Springfield.  Trees donated and decorated by businesses, civic and social organizations, schools, hospitals, families and individuals are raffled off at the conclusion of the event. Try your luck at winning your favorite! All proceeds of the event will help us to continue our 127 years of charitable work by providing children in the community with hope, opportunity, and a safe place to learn and grow. Get your FREE ticket at the William C. Sullivan Regional Visitor Center located at 1319 Main Street, conveniently located right across the street from the MassMutual Center.




December 1 – December 31 | Jess Miller’s OMG Comedy Club across from Theodore’s on Worthington St


Jess Miller Comedy presents The OMG Comedy Club, A Pop Up Comedy Club, across the street from Theodore’s on Worthington St in Springfield, Mass for the Month of December. Bring a toy and get $5 off any show! Order online with the promo code (must bring a toy with you to the show).




December 7 + December 14 | 10am – 5pm | Springfield Museums

Get ready for the big day with holiday-themed family activities. Free with museum admission! Activities are available December 7 and December 14, 2019.


December 12 | 5pm | Springfield Museums 

Mix up the weekday with a toast to culture, community and conversation!

Celebrate the season in the Gingerbread: Hollywood and the Holidays special exhibit, dress as your favorite holiday movie character, watch a gingerbread decorating demonstration with Chef Eric, and experience a special planetarium show. Plus music, festive hors d’oeuvres and cocktails!

Includes entertainment and hors d’oeuvres. Ages 21 and up. Advance purchase suggested.



All month long

Enjoy ice skating out on the Plaza, Igloo Experience at TAP Sports Bar and the Yuengling Beer shed, shopping at Kringle Candle, and much more.



Breakfast with Santa |  December 14 | 8:30am – 10am  

Enjoy Breakfast with Santa on Saturday, Dec. 14 from 8:30 – 10 am in MassMutual Center’s Ballroom. Guests can partake in pancakes, scrambled eggs, fruit and other favorites while meeting and greeting with Jolly Old Saint Nicholas! Proceeds will benefit the Springfield Boys & Girls Club.

Breakfast with Santa includes FREE admission to the following festivities: The Boys & Girls Club of Springfield’s 19th Annual Festival of Trees and  MassMutual Center’s 3rd Annual Wonderland Workshop

3rd Annual Wonderland Workshop December 14 | 9am – 3pm | MassMutual Center

MassMutual Center is hosting their 3rd Annual Wonderland Workshop to celebrate the holiday season. This family-friendly event will feature various interactive stations including cookie decorating, craft making and writing letters to Santa. Guests can indulge in one-of-a-kind treats and trinkets from local vendors displayed throughout the Wonderland Workshop’s holiday promenade. The Pioneer Valley’s country music radio station, KIX 100.9 will be on site with prizes and your chance to win tickets to upcoming MassMutual Center events. This event is free and open to the public. Families are encouraged to bring a new, unwrapped toy for a drive to benefit local charities.


The Office Holiday Party at the Springfield Thunderbirds

Saturday December 14 | 7pm | MassMutual Center

The Thunderbirds welcome Leslie David Baker – better known as “Stanley Hudson” from the popular NBC series “The Office”, for a special Holiday Party edition of T-Birds hockey! For more information on Baker’s appearance, including information on VIP Packages and other special ticket offerings, click here. 


Holiday Happenings at Tower Square

Holiday Open House – Tower Square will be continuing its tradition of hosting an Open House after the Tower Square Parade of the Big Balloons on Friday, November 29.

Holiday Fair at Tower Square – Tower Square is a toy drop off location for the Pioneer Valley USO.  The USO is collecting toys for children of military families again this year.




DECEMBER 15 @ 2:00 PM3:30 PM

Springfield Symphony Hall will be filled with the sounds of the holiday season as the Spirit of Springfield present a free holiday concert by the 215th Army Band of the Massachusetts Army National Guard 215th Army Band. Sponsored by Trinity Health Of New England and Mercy Medical Center, the performance will include holiday favorites as well as patriotic selections.




Have an event you’d like us to feature? Email!

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