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What to do in Pittsfield

Between Monday, November 17, 2025 and Friday, January 16, 2026

Enfield Community Chorus Winter Holiday Concert
Dec 13Enjoy a festive winter holiday concert by the Enfield Community Chorus.
Triumph Dealer Holiday Party
Dec 13A holiday party hosted by Triumph of Enfield.
Enfield Community Chorus Winter Holiday Concert
Dec 14Enjoy a festive winter holiday concert by the Enfield Community Chorus.
Decemberfest!
Dec 9A full-day event at Kingswood Oxford School.
Fireside Chat (Upper School, Grades 9-12)
Dec 10An informational fireside chat for prospective upper school students and their parents.
Northampton Historical Commission Meeting
Dec 15A public meeting of the Northampton Historical Commission.
Kimaya Diggs Holiday Show
Dec 19The fifth annual Kimaya Diggs & Friends holiday show.
Kingswood Oxford Middle School Walk & Talk
Dec 12An opportunity for prospective students and parents to walk and talk with admissions staff.
The Music of Prince ft. The Black Soul Experience
Dec 28A live music performance celebrating the music of Prince.
A Christmas Carol
Dec 27Hartford's beloved holiday tradition returns to the stage.
Polar Express Book Reading
Dec 15Book reading at the Hyde Park Railroad Station Museum.
A Minecraft Movie "Family Fun Day" Free Movie Screening
Dec 28Free screening of a Minecraft movie for a family fun day
moe. special guest Eastbound Jesus
Dec 28Live music performance by moe. with special guest Eastbound Jesus
Evening Capitol Tours for the Holidays
Dec 26Take a special holiday-themed tour of the historic New York State Capitol.
Capital Region Kwanzaa Celebration
Dec 26A local celebration marking Kwanzaa.
Schenectady Festival of Trees
Dec 22View a festive display of beautifully decorated Christmas trees.
Wednesday Team Trivia @ Emack & Bolio's Ice Cream
Dec 24Test your knowledge at a fun trivia night.
Holiday Story Time at the Mall
Dec 22Enjoy a special story time for children.
46th Annual Christmas Parlour Tour
Dec 22A tour of historic homes in Albany decorated for the holiday season.
Winter Light Walk
Dec 23Experience a festive display of lights.
Winter Old Capitol Farmer's Market
Dec 25A winter farmer's market offering local goods.
Stella Cole in Concert
Dec 23A concert performance by Stella Cole.
The Ice Rink at MGM Springfield
Dec 28Outdoor ice skating available at MGM Springfield.
The Ice Rink at MGM Springfield
Dec 27Outdoor ice skating available at MGM Springfield.
ROAR! Comedy: New England's Funniest
Dec 28A comedy show featuring New England's funniest comedians.
Springfield Thunderbirds vs. Providence Bruins
Dec 27An AHL hockey game between the Springfield Thunderbirds and the Providence Bruins.
Candlelight: Christmas Carols on Strings
Dec 27An enchanting evening featuring Christmas carols performed on strings.
Christmas Village at Westfir Lodge
Dec 27Enjoy live music, Christmas Carolers, shop the holiday market and visit with Santa.
Schenectady Festival of Trees
Dec 6A festival showcasing decorated trees