Events and Things to Do in Madison, CT

Sunday, October 18

Featured

ShoreCon 2: ALL Comic Book Show

OCT

18

10:00 AM

East Creek Landing, 390 S Union St, Guilford, CT

SHORECON 2: AN ALL COMIC BOOK SHOW RETURNS TO GUILFORD Over 30 tables at this one-day event. Guilford, Connecticut: ShoreCon is...

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Wednesday, October 21

Featured

Complimentary Presentation - Taking Control of Your Workplace Retirement Benefits

OCT

21

12:30 PM

Shelton-Derby, CT

During this complimentary session we’ll discuss why your future financial security and your retirement lifestyle depend on how...

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Friday, October 23

Featured

Portraits on the Farm

OCT

23

4:00 PM

Madison, CT

Seasonal photography on location in Madison at Seahorse Farm. The perfect setting for beautiful photographs. Charming barn,...

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Saturday, October 24

Featured

Farm Day at Down the Lane Farm

OCT

24

10:00 AM

18 Reservoir Rd, Killingworth, CT

Down the Lane Farm will host Farm Day on October 24 from 10 AM to 4 PM, welcoming the community for a fun fall day on the farm...

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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!...

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Featured

Portraits on the Farm

OCT

25

3:00 PM

Madison, CT

Seasonal photography on location in Madison at Seahorse Farm. The perfect setting for beautiful photographs. Charming barn,...

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Sunday, November 1

Featured

Demonstration of Mediumship: messages from loved ones in Spirit

NOV

1

1:00 PM

EBB and Flo Wellness, 365 E Main St, Branford, CT

Overview Experience an afternoon of spiritual connection, and messages from loved ones in Spirit. Join me, Paula Lowe, for a...

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Sunday, October 18

• ShoreCon 2: ALL Comic Book Show 10:00 am

  East Creek Landing, 390 S Union St, Guilford

  
  

Wednesday, October 21

• Complimentary Presentation - Taking Control of Your Workplace Retirement Benefits 12:30 pm

  Online Event

  
  

Thursday, October 22

• Call to Care Uganda Wine to Water Gala 6:00 pm

  Westbrook Elks Lodge, 142 Seaside Ave, Westbrook

  
  

Friday, October 23

• Portraits on the Farm 4:00 pm

  Sea Horse Farms

  
  
• The Creative Evolution of a Mural Artist | History Happy Hour 6:00 pm

  853 Boston Post Rd, Madison

  
  
• 6th Grade Graveyard Dance 7:00 pm

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

  
  

Saturday, October 24

• Farm Day at Down the Lane Farm 10:00 am

  18 Reservoir Rd, Killingworth

  
  
• Open House 9:30 am

  The Country School, 341 Opening Hill Rd, Madison

  
  
• Bats In Connecticut 11:00 am

  Meigs Point Nature Center, 1288 Boston Post Road, Madison

  
  
• Carriage House After Dark: An Adults-Only Halloween Event 5:00 pm

  The Carriage House, 96 Fair St, Guilford

  
  
• The Witch Tryal 7:00 pm

  North Madison Congregational, 1271 Durham Rd, Madison

  
  

Sunday, October 25

• Jay Day - Fall Family Festival 11:00 am

  Jay Estate, 210 Boston Post Rd, Rye

  
  
• Portraits on the Farm 3:00 pm

  Seahorse Farms

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

  107 Bradley Rd, Madison

  
  

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

  
  

Saturday, November 7

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

  14 Meeting House Ln, 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

  
  

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