Events and Things to Do in Chester, CT

Saturday, October 3

Featured

ONE: For Harmony, For Humanity · Community Preview Concert

OCT

3

5:00 PM

The Morgan School, 71 Killingworth Turnpike, Clinton, CT

What does UNITY mean to you? On Saturday, October 3, 2026, Angelface Records — founded by Clinton residents Joe and Angelica...

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Featured

11 Days: The Story of Operation Pineapple Express

OCT

3

7:00 PM

Madison, CT

Experience a powerful one-man, one-act play written and performed by Lt. Col. (Retired) Scott Mann, a U.S. Army Green Beret and...

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Saturday, October 10

Featured

Oktoberfest: A Fundraiser for Guilford VFW Post 7666

OCT

10

12:00 PM

Martin-Bishop Field, 111 Long Hill Rd, Guilford, CT

Been to an Oktoberfest already this year? There's always room for one more! Saturday, October 10 · 12–7 PM · Martin-Bishop...

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Saturday, October 3

• ONE: For Harmony, For Humanity · Community Preview Concert 5:00 pm

  The Morgan School, 71 Killingworth Turnpike, Clinton

  
  
• 11 Days: The Story of Operation Pineapple Express 7:00 pm

  Torp Theater in Davidson Hall, CCSU, New Britain

  
  
• Live Music: The Gibbons

  6:30 pm

  Little House Brewing Company, 16 Main Street, Chester

  
  

Sunday, October 4

• Little House at the Sunday Chester Market

  10:00 am

  Little House Brewing Company, 16 Main Street, Chester

  
  
• Open Mic Afternoons hosted by Dave Teneyck & Christina Meadows

  2:00 pm

  Little House Brewing Company, 16 Main Street, Chester

  
  

Wednesday, October 7

• Weekly Trivia: Binge Thinkin’ with Brendan Bell

  7:00 pm

  Little House Brewing Company, 16 Main Street, Chester

  
  

Thursday, October 8

• Live Music: Chelsea Lorraine — Little House Brewing Company

  6:30 pm

  Little House Brewing Company, 16 Main St, Chester

  
  

Saturday, October 10

• Oktoberfest: A Fundraiser for Guilford VFW Post 7666 12:00 pm

  Martin-Bishop Field, 111 Long Hill Rd, Guilford

  
  
• Electrify Your Drive! Free EV Car Show in Old Saybrook 12:00 pm

  Kathleen E. Goodwin Elementary School, 80 Old Boston Post Rd, Old Saybrook

  
  
• Women's Retreat at Camp Hazen

  9:00 am

  Camp Hazen YMCA, 204 West Main Street, Chester

  
  

Sunday, October 11

• Placing of a Witness Stone 11:45 am

  St John's Episcopal Church, 3 Cross St, Essex

  
  
• Little House at the Sunday Chester Market

  10:00 am

  Main Street, Chester

  
  

Wednesday, October 14

• Weekly Trivia: Binge Thinkin’ with Brendan Bell

  7:00 pm
  
  

Saturday, December 5

• 60th Annual Christmas Faire at Deep River Congregational Church on Saturday, Dec. 5! 8:30 am

  Congregational Church-Deep Rvr, 1 Church St, Deep River

  
  

Sunday, December 6

• The Middlesex Hospital Vocal Chords present a" Musical Holiday Celebration" 2:00 pm

  Portland Senior High School, 95 High St, Portland