Events and Things to Do in Woodbury-Middlebury, CT

Sunday, September 20

Featured

Community Appreciation Dinner

SEP

20

12:00 PM

VFW Post 201 Hall, 2205 Baldwin St, Waterbury, CT

Join VFW Post 201 for an afternoon honoring first responders and outstanding citizens from the greater Waterbury area. This...

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Tuesday, September 22

Featured

Beginner-Friendly Square Dance Lessons

SEP

22

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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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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Sunday, September 20

• Community Appreciation Dinner 12:00 pm

  VFW Post 201 Hall, 2205 Baldwin St, Waterbury

  
  
• High Holidays in Litchfield: No Membership Required, Everyone Welcome 6:00 pm
  
  

Monday, September 21

• High Holidays in Litchfield: No Membership Required, Everyone Welcome 10:00 am
  
  

Tuesday, September 22

• Beginner-Friendly Square Dance Lessons 7:30 pm

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

  
  

Wednesday, September 23

• Looking for a little inspiration in a world that feels increasingly divided? 8:00 pm
  
  

Thursday, September 24

• Women's Torah & Tea 11:30 am

  Chabad Lubavitch of Northwest CT, 69 West St, Litchfield

  
  

Friday, September 25

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

  On-Site Live Estate Auction - Under Tents - Extravaganza

  
  
• Poetry and Meditation 9:45 am

  Hollister House Garden, 300 Nettleton Hollow Rd, Washington

  
  

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

  
  
• 🕊️ Find Meaning. Find Joy. Find Herring. This Shabbat at Chabad 🍷🐟 9:30 am

  Chabad Lubavitch of Northwest CT, 69 West St, Litchfield

  
  
• The Art of Healing: Poetry as Recovery 10:30 am

  Woodbury Public Library, 269 Main St S, Woodbury

  
  

Sunday, September 27

• Remember Warsaw 1:00 pm

  Southbury Library, 100 Poverty Rd, Southbury

  
  

Wednesday, September 30

• Looking for a little inspiration in a world that feels increasingly divided? 8:00 pm

  Zoom Or Facebook Live

  
  

Thursday, October 1

• Women's Torah & Tea 11:30 am

  Chabad Lubavitch of Northwest CT, 69 West St, Litchfield

  
  

Wednesday, October 7

• Looking for a little inspiration in a world that feels increasingly divided? 8:00 pm
  
  

Thursday, October 8

• Women's Torah & Tea 11:30 am

  Chabad Lubavitch of Northwest CT, 69 West St, Litchfield

  
  

Saturday, October 10

• 🕊️ Find Meaning. Find Joy. Find Herring. This Shabbat at Chabad 🍷🐟 9:00 am

  Chabad Lubavitch of Northwest CT, 69 West St, Litchfield

  
  
• Orchid Harvest 2026 12:00 pm

  Sheraton Hartford South Hotel, 100 Capital Blvd, Rocky Hill

  
  

Friday, October 16

• Designer Purse Bingo 5:30 pm

  Hawk Ridge Winery, 28 Plungis Rd, Watertown