Events and Things to Do in Orange, CT

Friday, October 23

Featured

Devoted: A New Medicare Advantage Plan in CT!

OCT

23

2:00 PM

Milford Public Library, 57 New Haven Ave, Milford, CT

Okay Folks – A breath of fresh air has landed.A new Medicare Advantage carrier, Devoted, is entering into Connecticut for 2027....

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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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Tuesday, October 27

Featured

Which Medicare plan should you choose for 2027?

OCT

27

1:00 PM

Orange, CT

With plans changing and new options entering Connecticut, it's easy to feel unsure. Jim Lambert breaks down the 2027 Aetna...

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Wednesday, October 28

Featured

Virtual: Free College Admissions & Financial Aid Workshop

OCT

28

7:30 PM

Milford, CT

Reservations are required. To reserve your spot please click on the QR CODE Or go to www.adcollegefunding.com Please join us...

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Thursday, October 29

Featured

Is it better to get a Medicare Supplement or a Medicare Advantage?

OCT

29

6:30 PM

Milford, CT

Join Jim Lambert to explore which Medicare plan makes more sense for you. Many of your friends already chose a Medicare...

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Sunday, November 8

Featured

Author Event: Ethan Rutherford at Trumbull Library

NOV

8

2:00 PM

Trumbull Library: Main Branch, 33 Quality St, Trumbull, CT

Meet Connecticut author Ethan Rutherford for an afternoon of conversation about writing, publishing, and his acclaimed novel,...

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Monday, November 16

Featured

A new Medicare plan option has landed in Connecticut. Four ways to learn more.

NOV

16

6:00 PM

Milford Senior Citizen Center, 9 Jepson Dr, Milford, CT

New to us, but not new to Medicare. Devoted Health is already established in states across the country, and now it's expanding...

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Friday, October 23

• Devoted: A New Medicare Advantage Plan in CT! 2:00 pm

  Milford Public Library, 57 New Haven Ave, Milford

  
  
• Fall Wedding Band Bash 10:00 am

  Diamond Designs, 500 Boston Post Rd, Orange

  
  

Sunday, October 25

• Jay Day - Fall Family Festival 11:00 am

  Jay Estate, 210 Boston Post Rd, Rye

  
  

Tuesday, October 27

• Which Medicare plan should you choose for 2027? 1:00 pm

  Orange Community Center, 525 Orange Center Rd, Orange

  
  

Wednesday, October 28

• Virtual: Free College Admissions & Financial Aid Workshop 7:30 pm

  VIRTUAL

  
  

Thursday, October 29

• Is it better to get a Medicare Supplement or a Medicare Advantage? 6:30 pm

  St. Ann's Church Parish Hall, 501 Naugatuck Ave, Milford

  
  

Friday, October 30

• An Evening at the Haunted Manor 7:30 pm

  First United Church of Christ, 34 W Main St, Milford

  
  

Saturday, October 31

• Soundview Beer Works Halloween Spooktacular 5:00 pm

  230 Woodmont Rd, Milford

  
  

Tuesday, November 3

• Could a Medicare Supplement be your best choice? Come find out. 6:30 pm

  Total Mortgage Building's Conference Room, 185 Plains Rd, Milford, CT

  
  

Saturday, November 7

• Craft Fair 10:00 am

  High Plains Community Center, 525 Orange Center Rd, Orange

  
  

Sunday, November 8

• Author Event: Ethan Rutherford at Trumbull Library 2:00 pm

  Trumbull Library: Main Branch, 33 Quality St, Trumbull

  
  
• PYC Auxiliary Annual Fall Festival 11:00 am

  Pequonnock Yacht Club, 98 S Water St, New Haven

  
  

Monday, November 16

• A new Medicare plan option has landed in Connecticut. Four ways to learn more. 6:00 pm

  Milford Senior Citizen Center, 9 Jepson Dr, Milford

  
  
• Oil Painting Demo by Kathy Anderson 11:45 am

  Shelton Community Center, 41 Church Street, Shelton, CT, 2FL, Rm #2

  
  

Saturday, November 21

• John Ciambriello Plays Your Saturday Acoustic Playlist - Stappa Vineyard 2:30 pm

  Stappa Vineyard, 403 Derby Ave, Orange

  
  

Sunday, November 22

• Cheshire High School Train Show 10:00 pm

  Cheshire High School, 525 S Main St, Cheshire

  
  

Saturday, December 5

• Saint Raphael Parish's 2026 Christmas Fair 9:00 am

  501 Naugatuck Ave, Milford