Events and Things to Do in Cheshire, CT

Saturday, October 3

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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Sunday, October 4

Featured

The 10th Annual Fundraising Event Messages from Above - MHS Fundraiser

OCT

4

1:00 PM

North Italian Home Club, 43 Thorpe Ave, Meriden, CT

Please join us for an inspirational afternoon of connecting with loved ones in Heaven with Vanessa Lynn (published author of...

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Tuesday, October 6

Featured

Webinar Series for Solo Agers: Where Should I Live?

OCT

6

3:00 PM

Newington, CT

Don’t face overwhelming housing decisions alone. Choosing where to live as you age is one of the most important decisions...

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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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Sunday, October 18

Featured

Fall Open House - Notre Dame High School

OCT

18

10:00 AM

West Haven, CT

Fall Open House - 10:00amDiscover all that Notre Dame High School has to offer at our Fall Open House. Meet students, faculty,...

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Sunday, October 25

Featured

Haunt & Gather

OCT

25

11:00 AM

Mill Street Marketplace, 36 Mill St, Wethersfield, CT

Haunt & Gather is back for year two!! This is the one that leans fully into the season 😏 darker, a little witchy, and filled...

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Saturday, October 3

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

  Torp Theater in Davidson Hall, CCSU, New Britain

  
  

Sunday, October 4

• The 10th Annual Fundraising Event Messages from Above - MHS Fundraiser 1:00 pm

  North Italian Home Club, 43 Thorpe Ave, Meriden

  
  

Tuesday, October 6

• Webinar Series for Solo Agers: Where Should I Live? 3:00 pm

  Online

  
  

Thursday, October 8

• ACAP South Central MEDICARE MUST KNOWS for 2027 5:30 pm

  Masonicare At Ashlar Village, 74 Cheshire Rd, Wallingford

  
  

Saturday, October 10

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

  Martin-Bishop Field, 111 Long Hill Rd, Guilford

  
  

Sunday, October 11

• Redscroll Records Presents A Record Fair @ Counter Weight Brewing! 11:00 am

  Counter Weight Brewing Co, 7 Diana Ct, Cheshire

  
  

Monday, October 12

• Cheshire Academy Open House 9:30 am

  Cheshire Academy, 10 Main St, Cheshire

  
  

Sunday, October 18

• Fall Open House - Notre Dame High School 10:00 am

  Notre Dame High School, 1 Notre Dame Way, West Haven, CT, 06516

  
  

Sunday, October 25

• Haunt & Gather 11:00 am

  Mill Street Marketplace, 36 Mill St, Wethersfield

  
  

Thursday, October 29

• Brightpath Wallingford Not-So-Spooky Open House Night! 4:00 pm

  Brightpath Wallingford, 15 N Plains Industrial Rd, Wallingford

  
  

Saturday, November 7

• Holiday Arts and Crafts Fair 2026 9:00 am

  238 Washington St, Wallingford

  
  

Wednesday, November 11

• Cheshire Academy Open House 9:30 am

  Cheshire Academy, 10 Main St, Cheshire

  
  

Saturday, November 14

• Love Your Cookies 2:00 pm

  Columbus Lodge, 2630 Whitney Ave, Hamden

  
  

Saturday, December 5

• Cheshire Academy Open House 9:30 am

  Cheshire Academy, 10 Main St, Cheshire

  
  

Sunday, December 6

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

  Portland Senior High School, 95 High St, Portland