Events and Things to Do in Tarrytown-Sleepy Hollow, NY

Saturday, October 24

Featured

Ardsley Sports Card & Memorabilia Show

OCT

24

10:00 AM

Concord Road School, 2 Concord Rd, Ardsley, NY

Ever wondered what's inside those sealed card packs everyone's opening on YouTube? Ardsley's inaugural event with We the Hobby...

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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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Sunday, November 1

Featured

Beyond the Diagnosis, the Story: A Narrative Medicine Workshop

NOV

1

11:00 AM

Sarah Lawrence College, 1 Mead Way, Bronxville, NY

Close out Breast Cancer Awareness Month with an afternoon of conversation, tea, and writing. Narrative Medicine at Sarah...

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Saturday, December 19

Featured

Serenata Chamber Series: Serenata Solstice ~ Echoes of Light

DEC

19

7:00 PM

The Angel Nyack, 18 S Broadway, Nyack, NY

TICKETS Celebrate the Winter Solstice with an evening that moves through three transitions — Winter Comes, In the Darkness, A...

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Saturday, October 24

• Ardsley Sports Card & Memorabilia Show 10:00 am

  Concord Road School, 2 Concord Rd, Ardsley

  
  
• Pumpkins, Pipes & Peculiar Stories 4:00 pm

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

  
  
• Sleepy Hollow Halloween 10K & Kids FUN RUN 9:00 am

  Sleepy Hollow

  
  

Sunday, October 25

• Jay Day - Fall Family Festival 11:00 am

  Jay Estate, 210 Boston Post Rd, Rye

  
  
• Fall Fest 10:00 am

  Shames JCC on the Hudson, 371 S Broadway, Tarrytown

  
  
• Slapering Hol Press Presents the Debut Poets Reading 4:00 pm

  Hudson Valley Writers Center, 300 Riverside Dr, Sleepy Hollow

  
  

Monday, October 26

• The 2026 Rivertowns Pumpkin Trail Art Auction 9:00 am

  Sleepy Hollow and Tarrytown

  
  
• ACOTAR #6 Midnight Release Party at Transom Bookshop 11:59 pm

  Transom Bookshop, 23 Main St, Tarrytown

  
  

Tuesday, October 27

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

Friday, October 30

• Stevie's Blue Lamp: A Stevie Nicks Tribute Band 7:30 pm

  Shames JCC on the Hudson, 371 S Broadway, Tarrytown

  
  

Saturday, October 31

• Battle of the Boroughs: Halloween Breakin’ Bash 1:00 pm

  Montessori School 27, 132 Valentine Ln, Yonkers

  
  

Sunday, November 1

• Beyond the Diagnosis, the Story: A Narrative Medicine Workshop 11:00 am

  Sarah Lawrence College, 1 Mead Way, Bronxville

  
  

Monday, November 2

• Live Talks NY Presents An Evening with Andy Serkis 9:00 am

  Tarrytown Music Hall, 13 Main St, Tarrytown

  
  

Thursday, November 5

• Stevie's Blue Lamp: A Stevie Nicks Tribute Band 7:30 pm

  Shames JCC on the Hudson, 371 S Broadway, Tarrytown

  
  

Saturday, November 7

• Pocantico Hills Marathon & Half Marathon 8:00 am

  Rockwood Hall, Sleepy Hollow, NY 10591

  
  

Sunday, November 8

• Slapering Hol Press Presents the Annual War & Peace Reading (In-person) 4:00 pm

  Hudson Valley Writers Center, 300 Riverside Dr, Sleepy Hollow

  
  

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
  
  

Wednesday, November 11

• 2026 Outreach Clothing Sale! 10:00 am

  The Church of St. Barnabas, 15 N Broadway, Irvington