Events

Many events are planned for this upcoming year. You can find them Listed below.


225th Birthday Celebration
March 10th
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Earth Day Town Cleanup
April 21st
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Memorial Day Parade
May 28th
1:00 pm
Flyover by US Air Force 104th Fighter Wing


Eagles Band Community Concert
June 24th
3:00 pm
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Summer Choral Concert
June 29th
7:00 pm
St. Mary’s Church
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Appalachian Trail Celebration Day
June 30th
9:00 am – 1:00 pm
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Cheshire Cheese Fest
July 7th
11:00 am – 4:00 pm
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Visit Website


Music Block Party
July 11th
6:00 pm – 8:00 pm


Community Picnic & Boat Parade on Cheshire Lake
July 29th
12:00 pm (Picnic/Entertainment at Causeway)
1:00 pm (Boat Parade)
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Music Block Party
August 8th
6:00 pm – 8:00 pm


22nd Massachusetts Infantry Co D Encampment Demonstration
August 11th
9:00 am – 9:00 pm


Pittsfield Elms Vintage Baseball Club Demonstration
August 11th
1:00 pm


Cruz-Nite & Fireworks
August 11th
4:00 pm – 9:30 pm


Village Walking Tour – “What is and what was”
Thursday, August 23rd at 6:30pm
Sunday, August 26th at 2:00pm
Meet at Post Office


Cheshire Historical Slide Show Presentation
September 22nd
7:00 pm


Community Hike to Cheshire Cobbles
September 29th
10:00 am