Events and Things to Do in Pleasantville-Briarcliff Manor, NY

Thursday, October 22

Saturday, October 24

Featured

Pumpkins, Pipes & Peculiar Stories

OCT

24

4:00 PM

The Briarcliff Congregational Church, 30 S State Rd, Briarcliff Manor, NY

Join us for an evening of music and mystery presented by The Briarcliff Congregational Church. This atmospheric event features...

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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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Thursday, October 22

• NAACP Ossining Branch October General Meeting 7:00 pm

  Star of Bethlehem Church, 304 Spring St, Ossining

  
  

Friday, October 23

• Demystifying Medicare & Healthcare Coverage for Seniors 12:30 pm

  New Castle Community Center, 10 Senter St, Chappaqua

  
  

Saturday, October 24

• Pumpkins, Pipes & Peculiar Stories 4:00 pm

  The Briarcliff Congregational Church, 30 S State Rd, Briarcliff Manor

  
  

Sunday, October 25

• Jay Day - Fall Family Festival 11:00 am

  Jay Estate, 210 Boston Post Rd, Rye

  
  

Tuesday, October 27

• Join Hospital for Special Surgery (HSS) for a free webinar! 10:30 am
  
  

Wednesday, October 28

• Blood Drive 1:00 pm

  Thornwood Fire Department, 770 Commerce St, Thornwood

  
  

Saturday, October 31

• Demystifying Medicare & Healthcare Coverage for Seniors 10:00 am

  Mount Pleasant Public Library, 350 Bedford Rd, Pleasantville

  
  

Thursday, November 5

• Fall Blood Drive, Pleasantville High School – Thursday, Nov. 5, 2026 9:00 am

  Pleasantville High School, 60 Romer Ave, Pleasantville

  
  

Sunday, November 8

• 9in|9out Parent & Baby Expo 10:00 am

  Westchester Marriott, 670 White Plains Rd, Tarrytown

  
  

Tuesday, November 10

• Move with Confidence: Strength, Balance & Bone Health (Online Class) 10:00 am
  
  
• Medicare 2027: Know Your Rights: HSS Free Webinar! 10:15 am
  
  
• Free HSS Webinar: Midlife Changes, Metabolism, Bone, and Joint Health (Zoom) 6:30 pm
  
  

Tuesday, November 17

• Protecting Your Health: Hearing, Dizziness & Your Balance with HSS! 10:30 am
  
  

Saturday, November 21

• Excelsior Symphony Orchestra Fall Concert: Inspired by America 7:30 pm

  Hackley School, 293 Benedict Ave, Tarrytown

  
  

Sunday, March 14, 2027

• Quartetto di Cremona 3:00 pm

  Sleepy Hollow High School, Sleepy Hollow

  
  

Sunday, April 11, 2027

• Curtis on Tour: Dohnányi Sextet 3:00 pm

  Sleepy Hollow High School, Sleepy Hollow

  
  

Sunday, May 2, 2027

• Horszowski Trio 3:00 pm

  Sleepy Hollow High School, Sleepy Hollow