Events and Things to Do in Middlebury, CT

Sunday, May 3

Featured

Second Company Governor's Horse Guard's 2026 Spring Trail Ride

MAY

3

8:00 AM

Second Company Governor's Horse Guard Grounds, 4 Wildlife Dr, Newtown, CT

Saddle up and join the Second Company Governor's Horse Guard for a beautiful spring ride through scenic trails. This rain or...

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Tuesday, May 5

Featured

Region 15 LMES Student in Top 3 for 2026 National Jr. Ranger Title hosted by Jeff Corwin.

MAY

5

9:00 AM

Middlebury, CT

MIDDLEBURY, CT – Region 15 student Kataliena Prior is making waves on the national stage. A 3rd grade student at Long Meadow...

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Thursday, May 7

Featured

Remember Our Connecticut Fallen Heroes & Veterans in May & Support APK through The Great Give!

MAY

7

8:00 PM

Madison, CT

On May 6-7th, help us show off the generosity of the Greater New Haven Community and donate to APK through The Great Give!...

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Saturday, May 9

Featured

Southbury Green Expo 2026 Invites Community to Explore Sustainable Living

MAY

9

11:00 AM

Pomperaug Elementary School, 607 Main St S, Southbury, CT

​​​Southbury, CT — Residents of Southbury and surrounding communities are invited to attend the Southbury Green Expo 2026, a...

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Sunday, May 3

• Second Company Governor's Horse Guard's 2026 Spring Trail Ride 8:00 am

  Second Company Governor's Horse Guard Grounds, 4 Wildlife Dr, Newtown

  
  
• UCC Southbury Youth Host Raffle to Benefit Mission Work 9:30 am

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

  
  

Monday, May 4

• Adult Watercolor 10:30 am

  Middlebury Public Library, 30 Crest Road, Middlebury

  
  
• Family Movie - May the 4th Edition 1:00 pm

  Middlebury Public Library, 30 Crest Road, Middlebury

  
  

Tuesday, May 5

• Region 15 LMES Student in Top 3 for 2026 National Jr. Ranger Title hosted by Jeff Corwin. 9:00 am
  
  
• Virtual Author Talk - Radhi Devlukia-Shetty 2:00 pm

  Middlebury Public Library, 30 Crest Road, Middlebury

  
  

Thursday, May 7

• Remember Our Connecticut Fallen Heroes & Veterans in May & Support APK through The Great Give! 8:00 pm

  Southern Connecticut

  
  
• Virtual Author Talk - Marjan Kamali 7:00 pm

  Middlebury Public Library, 30 Crest Road, Middlebury

  
  

Saturday, May 9

• Southbury Green Expo 2026 Invites Community to Explore Sustainable Living 11:00 am

  Pomperaug Elementary School, 607 Main St S, Southbury