Events and Things to Do in Madison, CT

Sunday, October 25

Featured

Jay Day - Fall Family Festival

OCT

25

11:00 AM

Jay Estate, 210 Boston Post Rd, Rye, NY

Jay Day is our classic fall family festival held annually at the 23-acre award-winning Jay Estate with offerings for everyone!...

Share

Sunday, October 25

• Jay Day - Fall Family Festival 11:00 am

  Jay Estate, 210 Boston Post Rd, Rye

  
  
• WALK for Vista! Returns to Madison on October 25 9:00 am

  107 Bradley Rd, Madison

  
  
• Portraits on the Farm 3:00 pm

  Seahorse Farms

  
  

Friday, October 30

• Family & Friends Halloween Bingo 6:00 pm

  The Barn - Madison, CT, 8 Campus Dr, Madison

  
  

Sunday, November 1

• Demonstration of Mediumship: messages from loved ones in Spirit 1:00 pm

  EBB and Flo Wellness, 365 E Main St, Branford

  
  

Wednesday, November 4

• Complimentary Presentation - Strategies to Help You Make an Impact with Your Estate 12:30 pm

  Online Event

  
  

Saturday, November 7

• Madison Lantern Tour 2026: Our History, Our Stories 5:00 pm

  14 Meeting House Ln, Madison

  
  
• Family Astronomy Night, Meigs Point Nature Center, November 6, 7pm 7:00 pm

  Meigs Point Hammonasset Beach State Park, Madison, CT, 1288 Boston Post Rd, Madison

  
  

Friday, November 13

• “Tuning In” Large Scale Figurative Oil Painting Exhibition, Opening Nov. 13 2026 New Haven 4:30 pm

  EleMar New England, 99-107 Shelton Ave, New Haven

  
  

Wednesday, November 18

• Complimentary Presentation - Giving With a Purpose 12:30 pm

  Online Event

  
  

Sunday, November 22

• Cheshire High School Train Show 10:00 pm

  Cheshire High School, 525 S Main St, Cheshire

  
  

Friday, December 4

• Drama Works Theatre: The Sound Inside, 12/4-12/13 7:30 pm

  Drama Works Theatre Company, 323 Boston Post Rd, Old Saybrook

  
  

Saturday, December 5

• 60th Annual Christmas Faire at Deep River Congregational Church on Saturday, Dec. 5! 8:30 am

  Congregational Church-Deep Rvr, 1 Church St, Deep River

  
  

Sunday, December 6

• The Middlesex Hospital Vocal Chords present a" Musical Holiday Celebration" 2:00 pm

  Portland Senior High School, 95 High St, Portland

  
  

Wednesday, January 13, 2027

• Reboot: A Life-Changing Event 7:00 pm

  St. Margaret Catholic Church, 24 Academy St, Madison