Holiday Events

3rd Annual Ugly Sweater Pub Crawl


Thursday, December 5th

The third annual Ugly Sweater Pub Crawl will be taking over the downtown streets again for a fun night of downtown bar hopping and holiday shenanigans. Ugly sweaters are a MUST. The walking pub crawl will begin on Market Street/NOSH followed by stops at Nadim’s, 211 Worthington Street Pub, Smith’s, and The Fort.

Festival of Trees


November 29th - December 15th

We invite you to celebrate the holidays at the Springfield Boys & Girls Club’s 19th Annual Festival of Trees located at the MassMutual Center.  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!

Skating on the Plaza

Through the Winter

This winter,  MGM Springfield’s Plaza will transform into a winter wonderland. Visitors of all ages will welcome the snow’s arrival at The Plaza’s ice skating rink and enjoy pop-up activations—from a hot chocolate stand to photo opportunities with Santa Claus.

Wonderland Workshop


Saturday, December 8th

MassMutual Center is hosting our 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.

Events at the Springfield Museums


All Month Long

Experience the holiday season at the Museums! Starting the day after Thanksgiving, the Springfield Museums will offer dozens of programs. From The Lighting of the Quadrangle to Culture and Cocktails and much more. Most events are free with museums admission!

Holiday Celebration


December 7

Just hear those sleigh bells jingling, ring-ting-tingling too … it’s the Springfield Symphony Orchestra & Chorus’ Holiday Celebration, the perfect beginning to your holiday season. Maestro Nick Palmer returns with such audience favorites as “Rudolf the Red-Nosed Reindeer,” “Frosty the Snowman,” the ubiquitous “Sleigh Ride,” and more.

An SSO holiday concert wouldn’t be the same without the SSO Chorus, under the direction of our own Nikki Stoia. These talented choristers always bring joy to the holiday season.

Breakfast with Santa


December 2nd and December 9th

Sheraton’s Breakfast with Santa is back on December 2nd and December 9th! Enjoy a full buffet, free passes to The Festival of Trees, photos with Santa, and much more. Call The Springfield Sheraton at 413-263-2009 to make your reservations.

Springfield Santacon


Saturday, December 8th

Calling All Santas! Join The Young Professional Society of Greater Springfield and The Springfield Thunderbirds on Friday, December 8th for the second annual Springfield Santacon. Each ticket includes entry to the Springfield Thunderbirds game and a donation to charity. Dress Festive!

The Shops at Marketplace


All Month Long

This holiday season,  head to The Shops at Marketplace for unique and gorgeous gifts, a little self-pampering with a mini manicure or yoga, weekly events, and much more.

215th Army Band Holiday Concert


December 9th

The Spirit of Springfield proudly presents a FREE holiday concert by the 215th Army Band of the Massachusetts Army National Guard on Sunday, December 9th at 2pm in Symphony Hall. Tickets are available at Big Y World Class Markets, 1350 Main Street Security Desk, and the William C Sullivan Visitor Center.

Holiday Celebrations and Libations

Celebrate the holidays with your family and loved ones at any of our wonderful downtown restaurants. Whether it’s continuing your tradition at the Student Prince and enjoying their holiday carolers, reserving the large table in the front of Art e’ Pizza to watch the Christmas lights, or trying one of Max’s Tavern’s holiday drink specials. Come on down here and start making memories.