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

Sunday, September 20

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SeptemberFest 2026

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12:00 PM

Chappaqua-Mount Kisco, NY

Experience Mount Kisco's biggest block party featuring a carnival, live music, delicious food, and a vibrant street fair....

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Tuesday, September 22

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Protecting Your Health: Medications & Fall Risk: Free HSS Program!

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10:30 AM

Upper East Side, NY

Falls are a leading cause of injury among adults, and certain prescription and over-the-counter medications can increase the...

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Saturday, September 26

Featured

Improv Comedy Night at Hudson Valley Books for Humanity!

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9:00 PM

Hudson Valley Books for Humanity, 67 Central Ave, Ossining, NY

Join us for a wild, unscripted night of comedy featuring Blind Tiger Improv and their house teams Brunch Punk and Play It...

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Sunday, September 27

Featured

Silver Fest

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27

5:00 PM

Silver Pro Music, 183 S Central Ave, Hartsdale, NY

A fundraiser benefitting Rivertown Dance Academy, a 501(c)3 profit organization. Gather with us on September 27 to celebrate...

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Sunday, September 20

• SeptemberFest 2026 12:00 pm

  Mount Kisco, Mt Kisco

  
  

Tuesday, September 22

• Protecting Your Health: Medications & Fall Risk: Free HSS Program! 10:30 am
  
  

Thursday, September 24

• Taconic Opera’s 2026 Annual Gala: Opera Goes to Church 7:00 pm

  Caperberry Events @ CV Rich Mansion, 305 Ridgeway, White Plains

  
  

Friday, September 25

• Meet Bestselling Horror Writer Keith Rosson 3:00 pm

  Transom Bookshop, 23 Main St, Tarrytown

  
  
• Arc Stages presents The Last Five Years, starting Sept 25 7:00 pm

  Arc Stages, 147 Wheeler Ave, Pleasantville

  
  

Saturday, September 26

• Improv Comedy Night at Hudson Valley Books for Humanity! 9:00 pm

  Hudson Valley Books for Humanity, 67 Central Ave, Ossining

  
  
• Arc Stages presents The Last Five Years, starting Sept 25 7:00 pm

  Arc Stages, 147 Wheeler Ave, Pleasantville

  
  

Sunday, September 27

• Silver Fest 5:00 pm

  Silver Pro Music, 183 S Central Ave, Hartsdale

  
  
• Croton Rotary Auto Show 11:00 am

  Croton-Harmon Train Station Parking Lot, 4 Veterans Plaza, Croton-On-Hudson

  
  

Thursday, October 1

• Residential Landscape - Perfection Reimagined. Embracing the New Garden Ethos 10:30 am

  Pleasantville Presbyterian Church, 400 Bedford Rd, Pleasantville

  
  

Saturday, October 3

• Pleasantville Farmers Market Annual Apple Pie Contest 8:15 am

  Memorial Plaza, Pleasantville

  
  

Sunday, October 4

• BriarClefs A Cappella: FREE performance, Briarcliff Manor, Sunday, October 4, 2026, 3:00–4:00 PM! 9:00 am

  Scarborough Presbyterian Church, 655 Scarborough Rd, Briarcliff Manor

  
  
• The Balourdet Quartet 3:00 pm

  Sleepy Hollow High School, Sleepy Hollow

  
  

Wednesday, October 7

• Staying Strong Through Midlife and Beyond: HSS Free Webinar! 6:30 pm
  
  

Friday, October 9

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

  Bedford Hills Community House, 74 Main St, Bedford Hills

  
  

Saturday, October 10

• Market Day Crafts Fair in Fishkill 11:00 am

  Van Wyck Homestead Museum, 504 US-9, Fishkill

  
  

Monday, October 12

• Move with Confidence: The Nutrition Connection (In Person Class) 10:00 am

  Hospital for Special Surgery Main Hospital, 535 E 70th St, New York

  
  

Thursday, October 15

• Demystifying Medicare & Healthcare Coverage for Seniors 9:45 am

  Greenburgh Public Library, 300 Tarrytown Rd, Elmsford

  
  

Saturday, October 17

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

  Briarcliff Manor Public Library, 1 Library Rd, Briarcliff Manor

  
  

Sunday, October 18

• Trio Azura 3:00 pm

  Sleepy Hollow High School, Sleepy Hollow