Events and Things to Do in Cheshire, CT

Saturday, October 17

Featured

In The Lyman Light – Marching Band Competition

OCT

17

5:00 PM

Lyman Hall High School, 70 Pond Hill Rd, Wallingford, CT

The Lyman Hall Marching Band’s home show will take place on Saturday, Oct. 17, at Lyman Hall High School. The event features 14...

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Sunday, October 18

Featured

Fueling Futures Car Show

OCT

18

9:00 AM

St. Luke Catholic School, 133 Bristol St, Southington, CT

Our second car show for the benefit of St. Luke School.  Come and fill our tremendous parking lot with your show cars!  Cars...

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Featured

ShoreCon 2: ALL Comic Book Show

OCT

18

10:00 AM

East Creek Landing, 390 S Union St, Guilford, CT

SHORECON 2: AN ALL COMIC BOOK SHOW RETURNS TO GUILFORD Over 30 tables at this one-day event. Guilford, Connecticut: ShoreCon is...

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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

Jay Day - Fall Family Festival

OCT

25

11:00 AM

Jay Estate, 210 Boston Post Rd, Rye, NY

Jay Day is our classic fall family festival held annually at the 23-acre award-winning Jay Estate with offerings for everyone!...

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Saturday, October 17

• In The Lyman Light – Marching Band Competition 5:00 pm

  Lyman Hall High School, 70 Pond Hill Rd, Wallingford

  
  
• The Billy Joel and Elton John Experience: A Tribute to Billy Joel and Elton John. 6:00 pm

  Joseph A DePaolo Middle School, 385 Pleasant St, Southington

  
  

Sunday, October 18

• Fueling Futures Car Show 9:00 am

  St. Luke Catholic School, 133 Bristol St, Southington

  
  
• ShoreCon 2: ALL Comic Book Show 10:00 am

  East Creek Landing, 390 S Union St, Guilford

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

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

  
  

Saturday, October 24

• The Myriad Project: Fable & Fantasy 2:00 pm

  Quinnipiac University, 275 Mt Carmel Ave, Hamden

  
  

Sunday, October 25

• Jay Day - Fall Family Festival 11:00 am

  Jay Estate, 210 Boston Post Rd, Rye

  
  

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

  
  
• Read Across The World 11:00 pm

  Wallingford Elks Lodge #1365, 148 S Main 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

  
  

Sunday, November 22

• Cheshire High School Train Show 10:00 pm

  Cheshire High School, 525 S Main St, Cheshire

  
  

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