Events and Things to Do in Madison, CT

Wednesday, May 20

Featured

Complimentary Presentation - Smart Strategies for College Financing

MAY

20

12:30 PM

Shelton-Derby, CT

Whether your child is in grade school or applying to colleges now, it’s never too early - or too late - to start planning for...

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Friday, May 22

Featured

Javier Arau Jazz Quintet & Guilford High School Jazz Ensemble

MAY

22

7:00 PM

Guilford High School, 605 New England Rd, Guilford, CT

Come for an evening of great jazz music with the Guilford High School Jazz Ensemble, along with special guests, the Javier Arau...

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Saturday, May 23

Featured

Step Into a Fairytale

MAY

23

1:00 PM

Shubert Theatre, 247 College St, New Haven, CT

New Haven Ballet Presents The Sleeping Beauty at the Shubert Theatre This spring, New Haven Ballet invites audiences across...

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Saturday, May 30

Featured

2026 Guilford House Tour

MAY

30

10:00 AM

Guilford, CT

The Guilford House Tour returns, Saturday, May 30, 2026, from 10:00 AM to 4:00 PM, showcasing the insides of unique historic...

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Wednesday, May 20

• Complimentary Presentation - Smart Strategies for College Financing 12:30 pm

  Online Presentation

  
  

Friday, May 22

• Javier Arau Jazz Quintet & Guilford High School Jazz Ensemble 7:00 pm

  Guilford High School, 605 New England Rd, Guilford

  
  
• The Barn Bingo Night 6:30 pm

  Madison Arts Barn, 8 Campus Dr, Madison

  
  

Saturday, May 23

• Step Into a Fairytale 1:00 pm

  Shubert Theatre, 247 College St, New Haven

  
  

Tuesday, May 26

• 20th Annual Madison Exchange Club Golf Classic 12:30 pm

  Madison Country Club, 8 W Wharf Rd, Madison

  
  

Friday, May 29

• 4th Grade Dance Into Summer Social 6:00 pm

  The Madison Arts Barn, 8 Campus Dr, Madison

  
  
• The Liar Show 7:00 pm

  The Marketplace, 77 Whitfield St, Guilford

  
  

Saturday, May 30

• 2026 Guilford House Tour 10:00 am

  Guilford Town Green

  
  
• Healthy Kids Day 11:00 am

  Valley Shore YMCA, 201 Spencer Plains Rd, Westbrook

  
  
• Downtown Walking Tour of Madison, CT – May 30 1:00 pm

  853 Boston Post Rd, Madison

  
  

Friday, June 5

• Welcome to the Shoreline Men Over Sixty !!! 9:00 am

  26 Meeting House Lane, Madison, CT 06443

  
  

Saturday, June 6

• Madison Lions Day Flea Market 9:00 am

  Madison Green Historic District, Madison

  
  
• Accessory Dwelling Units (ADUs) - Educational Overview by Local Builder 12:00 pm

  E.C. Scranton Memorial Library, 801 Boston Post Rd, Madison

  
  
• Downtown Walking Tour of Madison, CT – June 6 1:00 pm

  853 Boston Post Rd, Madison

  
  

Tuesday, June 16

• Aphasia Presentation 4:00 pm

  E.C. Scranton Memorial Library, 801 Boston Post Rd, Madison

  
  

Friday, June 19

• Drama Works Theatre: The Aliens by Annie Baker 7:30 pm

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

  
  

Monday, June 22

• Country School Summer Fun and Learning Camp 9:00 am

  The Country School, 341 Opening Hill Rd, Madison

  
  

Monday, September 28

• Tip-A-Cop hosted by Branford Police Department to benefit Special Olympics Connecitcut 12:00 pm

  Lenny's Indian Head Inn, 205 S Montowese St, Branford