Events and Things to Do in Middletown, CT

Wednesday, December 17

Featured

Holiday Sip & Shop

DEC

17

5:00 PM

The 1851, 150 Sebethe Dr, Cromwell, CT

Join us at The 1851 and sip while you shop for the holidays with local vendors, farms and artisans on Wednesday, December 17th...

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Monday, January 5, 2026

Featured

Winter classes in Theater, Circus and Dance for kids ages 1 - 20

JAN

5

4:30 PM

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

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

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Tuesday, December 16

• 🎶 Mo Andres Live @ Klekolo World Coffee 🎶 7:00 pm

  Klekolo World Coffee, 181 Court St, Middletown

  
  

Wednesday, December 17

• Holiday Sip & Shop 5:00 pm

  The 1851, 150 Sebethe Dr, Cromwell

  
  

Friday, December 19

• Friday Night Live Music Series Featuring Alisa & Company at 1741 Pub & Grill 6:00 pm

  1741 Pub and Grill, 72 Lyman Rd, Middlefield

  
  

Saturday, December 20

• December 20 @ 10:00 am - December 21 @ 2:30 pm 10:00 am

  The Lyman Homestead, 3 Lyman Rd, Middlefield

  
  
• Santa Brunch at 1741 Pub & Grill 10:00 am

  1741 Pub and Grill, 72 Lyman Rd, Middlefield

  
  

Sunday, December 21

• A Child's Christmas in Wales 2:00 am

  The Buttonwood Tree, 605 Main St, Middletown

  
  
• Meditation & Talk Sundays 9:00 am

  343 Washington Terrace, Middletown

  
  
• Holiday Magic at Lyman Orchards 10:00 am

  The Lyman Homestead, 3 Lyman Rd, Middlefield

  
  
• Santa Brunch at 1741 Pub & Grill 10:00 am

  1741 Pub and Grill, 72 Lyman Rd, Middlefield

  
  
• Bonsai Workshop at BarrelHouse - Killingworth 1:00 pm

  BarrelHouse, 176 CT-81, Killingworth

  
  
• Kid's Gingerbread House Decorating Workshop at Lyman Orchards 1:00 pm

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

  
  

Monday, December 22

• Christmas Sing-A-Long Night with DJ Heartbeat at 1741 Pub & Grill 6:00 pm

  1741 Pub and Grill, 72 Lyman Rd, Middlefield

  
  

Friday, December 26

• Friday Night Live Music Series Featuring Shawn Taylor at 1741 Pub & Grill 6:00 pm

  1741 Pub and Grill, 72 Lyman Rd, Middlefield

  
  

Sunday, December 28

• All-You-Can-Eat Cider Pancake Sunday Brunch at 1741 Pub & Grill 10:00 am

  1741 Pub and Grill, 72 Lyman Rd, Middlefield

  
  

Tuesday, December 30

• Kid's Apple Pie Workshop During Winter Break at Lyman Orchards 10:00 am

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

  
  
• 🎸 Robi Polgar: Americana Soul with British Invasion Swagger Live @ Klekolo 🎤 7:00 pm

  Klekolo World Coffee, 181 Court St, Middletown

  
  

Wednesday, December 31

• New Year's Eve Celebration at 1741 Pub & Grill 6:00 pm

  1741 Pub and Grill, 72 Lyman Rd, Middlefield

  
  

Monday, January 5, 2026

• Winter classes in Theater, Circus and Dance for kids ages 1 - 20 4:30 pm

  Oddfellows Playhouse Youth Theater, 128 Washington St, Middletown

  
  

Tuesday, January 6, 2026

• 🎵 The Rumble Strips LIVE @ Klekolo World Coffee 🎵 7:00 pm

  Klekolo World Coffee, 181 Court St, Middletown

  
  

Wednesday, January 7, 2026

• Scottish Dancing in Middletown 7:15 pm

  190 Court St, Middletown, CT, 06457