Events and Things to Do in Middlebury, CT

Friday, September 25

Featured

"Big Earl's" Remarkable Estate Auction Sale

SEP

25

10:00 AM

Woodbury-Middlebury, CT

The Estate Collection of The Late “Big Earl” L. Postol Auction | September 25, 26, 27, 2026 • 10am to 5pm each day On-Site Live...

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Saturday, September 26

Featured

Apple Festival

SEP

26

10:00 AM

South Britain Congregational Church, 693 S Britain Rd, Southbury, CT

It’s APPLE FESTIVAL time Sept 26  10am-3pm! Join us for a fun-filled day of food, shopping, music, and family fun at our Annual...

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Featured

Region 15 Invites Community to STEM-A-Palooza!

SEP

26

10:00 AM

234 Judd Rd, Southbury, CT

Region 15 Schools is excited to invite the community to STEM-A-Palooza, a FREE day of hands-on exploration, activities and...

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Friday, October 16

Featured

Designer Purse Bingo

OCT

16

5:30 PM

Hawk Ridge Winery, 28 Plungis Rd, Watertown, CT

Join Literacy Volunteers of Greater Waterbury for Designer Purse Bingo on Friday, October 16, at Hawk Ridge Winery in...

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Thursday, September 24

• Virtual Author Talk - Lucky Diaz 7:00 pm

  Middlebury Public Library, 30 Crest Road, Middlebury

  
  
• OCM Festival String Quartet

  7:30 pm

  Town Hall Theater, 72-76 Merchants Row, Middlebury

  
  

Friday, September 25

• "Big Earl's" Remarkable Estate Auction Sale 10:00 am

  On-Site Live Estate Auction - Under Tents - Extravaganza

  
  
• LMES - Back-to-School Ice Cream Social 5:45 pm

  LMES Field, Middlebury

  
  
• The Loop: The Conversations Trio

  6:00 pm

  Town Hall Theater, 72-76 Merchants Row, Middlebury

  
  

Saturday, September 26

• Apple Festival 10:00 am

  South Britain Congregational Church, 693 S Britain Rd, Southbury

  
  
• Region 15 Invites Community to STEM-A-Palooza! 10:00 am

  234 Judd Rd, Southbury

  
  
• Rooted In Woodbury: Understanding, Protecting, and Caring for Our Trees 10:00 am

  Sugar House @ Flanders Nature Center, 48 Church Hill Rd, Woodbury, CT, 06798

  
  
• The Addison String Quartet

  11:00 am

  Town Hall Theater, 72-76 Merchants Row, Middlebury

  
  

Sunday, September 27

• Music and Social Power: How Has Music Shaped American Culture? How Does American Culture Shape Music?

  2:00 pm

  Town Hall Theater, 72-76 Merchants Row, Middlebury

  
  
• Issue 21. Release Party

  4:00 pm

  Town Hall Theater, 72-76 Merchants Row, Middlebury

  
  

Friday, October 16

• Designer Purse Bingo 5:30 pm

  Hawk Ridge Winery, 28 Plungis Rd, Watertown

  
  

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