Events and Things to Do in Middletown, CT

Wednesday, September 9

Featured

Tim Eriksen & Peter Irvine

SEP

9

7:30 PM

Middletown, CT

Tim Eriksen is a highly regarded singer of American folksong and shapenote music, a songwriter whose work has been covered by...

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Thursday, September 10

Featured

String of Pearls Big Band - Dinner and Dancing!

SEP

10

5:00 PM

Casa Mia at the Hawthorne, 2421 Berlin Tpke, Berlin, CT

Enjoy the sounds of the Big Band Era and The Great American Songbook along with a world-class dining experience.  No Cover-No...

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Saturday, September 12

Featured

Connecticut Bead Society Annual Bead Bazaar This Saturday, Sept. 12!

SEP

12

10:00 AM

Elks Lodge #771, 44 Maynard St, Middletown, CT

Gather, create, and be inspired at The Connecticut Bead Society's Annual Bead Bazaar! This vibrant event features various...

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Featured

Oddfellows Playhouse Fall Programming for ages 1 to 20 begins September 12, 2026

SEP

12

9:00 PM

Oddfellows Playhouse Youth Theater, 128 Washington St, Middletown, CT

Registration is now open for Fall Classes at Oddfellows Playhouse Youth Theater, located at 128 Washington Street in...

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Saturday, September 19

Featured

Jay Medal Soirée

SEP

19

5:30 PM

Jay Estate, 210 Boston Post Rd, Rye, NY

The Jay Heritage Center in Rye, New York will celebrate America at 250 with a toast to Jay Medal honorees Pulitzer...

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Sunday, September 20

Featured

Brews for Boats

SEP

20

4:00 PM

Concentric Brewing Company, 91 Main St, Portland, CT

centralctrowing.com/events

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Monday, September 7

• Goat Cuddle Brigade at Lyman Orchards 10:00 am

  Lyman Orchards Apple Barrel Farm Market, 32 Reeds Gap Rd, Middlefield

  
  
• Horse-Drawn Wagon Rides & Trackless Train 10:00 am

  Lyman Orchards Golf Club, 70 Lyman Rd, Middlefield

  
  
• Seeds to Success: Children's Entrepreneurial Market 11:00 am

  Lyman Orchards Apple Barrel Farm Market, 32 Reeds Gap Rd, Middlefield

  
  

Tuesday, September 8

• Sing with GMChorale! 6:45 pm

  Bethany Lutheran Church, 50 Court St., Cromwell, CT

  
  
• 🎵 PJ Childs⁠ Live - Klekolo Sesssions⁠ 7:00 pm

  Klekolo World Coffee, 181 Court St, Middletown

  
  

Wednesday, September 9

• Tim Eriksen & Peter Irvine 7:30 pm

  Middletown House Concert Series

  
  

Thursday, September 10

• String of Pearls Big Band - Dinner and Dancing! 5:00 pm

  Casa Mia at the Hawthorne, 2421 Berlin Tpke, Berlin

  
  
• Full Moon Sound Meditation at Lyman Orchards 6:00 pm

  1741 Pub and Grill, 72 Lyman Rd, Middlefield

  
  
• David Borges, "UConn Basketball: An Illustrated Timeline" 6:00 pm

  Wesleyan RJ Julia Bookstore, 413 Main St, Middletown

  
  

Friday, September 11

• Twilight Hard Cider Maze at Lyman Orchards Corn Maze 5:00 pm

  Lyman Orchards Corn Maze, 32 Reeds Gap Rd, Middlefield

  
  
• Friday Night Live Music Series Featuring Brother Other Under the Tent at 1741 Pub & Grill 6:00 pm

  1741 Pub and Grill, 72 Lyman Rd, Middlefield

  
  

Saturday, September 12

• Connecticut Bead Society Annual Bead Bazaar This Saturday, Sept. 12! 10:00 am

  Elks Lodge #771, 44 Maynard St, Middletown

  
  
• Oddfellows Playhouse Fall Programming for ages 1 to 20 begins September 12, 2026 9:00 pm

  Oddfellows Playhouse Youth Theater, 128 Washington St, Middletown

  
  
• Redeemables for Vets & Neighbors 8:00 am

  Ace Hardware, 480 S Main St, Middletown

  
  
• Corn Maze & Cider Donut Harvest Music Festival 10:00 am

  Lyman Orchards Apple Barrel Farm Market, 32 Reeds Gap Rd, Middlefield

  
  
• Board Game Tag Sale 10:00 am

  Back Again Board Game Cafe LLC, 484 Main St, Middletown

  
  
• The Beer Garden at the Corn Maze & Cider Donut Harvest Music Festival 12:00 pm

  Lyman Orchards Apple Barrel Farm Market, 32 Reeds Gap Rd, Middlefield

  
  

Sunday, September 13

• Meditation & Talk Sundays 9:00 am

  343 Washington Terrace, Middletown

  
  
• Corn Maze & Cider Donut Harvest Music Festival 10:00 am

  Lyman Orchards Apple Barrel Farm Market, 32 Reeds Gap Rd, Middlefield

  
  
• The Beer Garden at the Corn Maze & Cider Donut Harvest Music Festival 12:00 pm

  Lyman Orchards Apple Barrel Farm Market, 32 Reeds Gap Rd, Middlefield