Events and Things to Do in Cheshire, CT

Saturday, September 19

Featured

Sidewalk Sale - September 18th-20th

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9:30 AM

Newbury Place, 41 Oak Tree Rd, Southbury, CT

We need to make room for Holiday Merchandise!  Stop by all weekend, starting Friday, September 18th, for our Annual Sidewalk Sale.

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Featured

America at 250 for Educators

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19

3:30 PM

Jay Heritage Center, 210 Boston Post Rd, Rye, NY

The Jay Heritage Center (JHC) is proud to welcome educators and the general public to our site during September 2026,...

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Tuesday, September 22

Featured

Beginner-Friendly Square Dance Lessons

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7:30 PM

The United Church of Christ Southbury, 283 Main St N, Southbury, CT

Looking for low-impact exercise and a fun way to meet new friends? Learn to Square Dance!  Beginner-Friendly Square Dance...

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Wednesday, September 23

Featured

Virtual: Free College Admissions & Financial Aid Workshop

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8:30 PM

Wallingford, CT

Reservations are required. To reserve your spot please click on the QR CODE Or go to www.adcollegefunding.com Please join us...

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Thursday, September 24

Featured

14th Annual Latino Winemakers Wine Tasting

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5:30 PM

The Farms Country Club, 180 Cheshire Rd, Wallingford, CT

Join us for our annual wine tasting featuring selections from South America, Spain, and California, paired with delicious food...

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Saturday, September 19

• Sidewalk Sale - September 18th-20th 9:30 am

  Newbury Place, 41 Oak Tree Rd, Southbury

  
  
• America at 250 for Educators 3:30 pm

  Jay Heritage Center, 210 Boston Post Rd, Rye

  
  

Monday, September 21

• Wellness Talk: Wellness and Movement with Heather Chandor 7:00 pm

  First Congregational Church, 111 Church Dr, Cheshire

  
  

Tuesday, September 22

• Beginner-Friendly Square Dance Lessons 7:30 pm

  The United Church of Christ Southbury, 283 Main St N, Southbury

  
  
• Congregation Mishkan Israel, 785 Ridge Rd, Hamden, CT, 06517 6:15 pm

  Silk 'n Sounds Inc

  
  

Wednesday, September 23

• Virtual: Free College Admissions & Financial Aid Workshop 8:30 pm

  Virtual

  
  
• Cheshire Art League Sept. Speaker 6:30 pm

  Cheshire Public Library, 104 Main St, Cheshire

  
  

Thursday, September 24

• 14th Annual Latino Winemakers Wine Tasting 5:30 pm

  The Farms Country Club, 180 Cheshire Rd, Wallingford

  
  

Sunday, October 4

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

  North Italian Home Club, 43 Thorpe Ave, Meriden

  
  

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

  
  

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