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Visit Sleepy Hollow

Where the Legend Lives

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  • See
    • Christ Episcopal Church
    • Headless Horseman Bridge
    • Headless Horseman Statue
    • Historical Society
    • Kykuit
    • Legend Landmarks
    • Lyndhurst
    • Octagon House
    • Old Croton Aqueduct Trail
    • Old Dutch Church
    • Philipsburg Manor
    • Rockefeller State Park Preserve 
    • Sleepy Hollow Cemetery
      • Sleepy Hollow Cemetery Tours
    • Sleepy Hollow Lighthouse
    • Sunnyside
    • Union Church of Pocantico Hills
  • Events
    • Events Calendar
    • Halloween in Sleepy Hollow
    • Jazz Forum
    • Tarrytown Music Hall Performances
    • Sunset Jazz at Lyndhurst Summer Series
  • Shop
    • Farmers Markets
    • Sleepy Hollow Souvenirs
  • Dine
    • Breakfast
    • Lunch and Dinner
    • Drinks
    • Coffee & Tea
    • Sweets
  • Stay
    • Hotels
    • Motels and Budget
    • Inns and Bed & Breakfasts
    • Camping
  • About
    • How Charles Dickens Stole Christmas
    • Movies Made Here
    • Florence Inn
    • Directions
Headless horseman buttons and coasters displayed for sale at the annual Sleepy Hollow Street Fair.

Sleepy Hollow Street Fair

J & G Deli's food tent is one of the popular stops at the annual Sleepy Hollow Street Fair.

The Sleepy Hollow Tarrytown Chamber of Commerce’s annual Sleepy Hollow Street Fair takes place this year on Saturday, October 8th, transforming Beekman Avenue into an outdoor market.

October is the most exciting time to visit Sleepy Hollow. The weeks leading up to Halloween have something for everyone: haunted hayrides, Gothic mansions, blazing pumpkins, farmers markets, live music, 5K run (costumes welcome!), Halloween parade, and of course, the Headless Horseman! If your visit includes the second weekend of October, be sure to stop by the Sleepy Hollow Street Fair where you will find food, music, local retailers, arts & crafts, plus Halloween and Holiday items!

Explore more local shopping at Tarrytown’s and Sleepy Hollow’s galleries, gift shops and antique stores.

2022 Date: October 8, 10 am to 4 pm.

Where: Beekman Avenue, Sleepy Hollow, NY 10591 (Between Pocantico Street and Broadway)

For info: 914-631-1705, https://www.sleepyhollowtarrytownchamber.com

Category: 2022 Events

Previous Post: «A performer with Westchester Circus Arts performs on aerial silks. The Legend – Cirque Theatre Performance
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  • Week of March 26
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2:00 pm
March 26 @ 2:00 pm - 3:30 pm Event Series

Tartuffe

Lyndhurst 635 South Broadway, Tarrytown
$45
4:00 pm
March 26 @ 4:00 pm - 5:00 pm Event Series

Neal Spitzer & Friends

Jazz Forum Club 1 Dixon Lane, Tarrytown
$15 – $20
6:00 pm
March 26 @ 6:00 pm - 7:00 pm Event Series

Neal Spitzer & Friends

Jazz Forum Club 1 Dixon Lane, Tarrytown
$15 – $20
+ 1 More
  • No events scheduled for March 27, 2023.
  • No events scheduled for March 28, 2023.
  • No events scheduled for March 29, 2023.
  • No events scheduled for March 30, 2023.
7:00 pm
March 31 @ 7:00 pm - 8:30 pm Event Series

Anthony Rodia

Tarrytown Music Hall 13 Main Street, Tarrytown
$40 – $65
9:00 pm
March 31 @ 9:30 pm - 11:00 pm Event Series

Anthony Rodia

Tarrytown Music Hall 13 Main Street, Tarrytown
$40 – $65
9:00 am
April 1 @ 9:30 am - 4:00 pm Event Series

Lyndhurst Tours

Lyndhurst 635 South Broadway, Tarrytown
$18 – $42
8:00 pm
April 1 @ 8:00 pm - 9:30 pm

The Manhattan Transfer 50th Anniversary

Tarrytown Music Hall 13 Main Street, Tarrytown
$55 – $85

Week of Events

Sun 26

Mon 27

Tue 28

Wed 29

Thu 30

Fri 31

Sat 1

2:00 pm - 3:30 pm Event Series

Tartuffe

March 26 @ 2:00 pm - 3:30 pm Event Series

Tartuffe

M&M Performing Arts brings Tartuffe, Molière’s timely, classic farce about seduction, hypocrisy, and deception, in a ridiculously hilarious new adaptation to Lyndhurst Mansion in March 2023. The funniest play on Broadway …

$45
4:00 pm - 5:00 pm Event Series

Neal Spitzer & Friends

March 26 @ 4:00 pm - 5:00 pm Event Series

Neal Spitzer & Friends

Neal Andrew Spitzer is a full time musician, composer, educator and sound engineer. Music has always been a big part of Neal Spitzer's life as his mother, the accomplished concert …

$15 – $20
6:00 pm - 7:00 pm Event Series

Neal Spitzer & Friends

March 26 @ 6:00 pm - 7:00 pm Event Series

Neal Spitzer & Friends

Neal Andrew Spitzer is a full time musician, composer, educator and sound engineer. Music has always been a big part of Neal Spitzer's life as his mother, the accomplished concert …

$15 – $20
+ 1 More
7:00 pm - 8:30 pm Event Series

Anthony Rodia

March 31 @ 7:00 pm - 8:30 pm Event Series

Anthony Rodia

A first-generation Italian-American born and raised right here in Westchester County, New York, Anthony Rodia came out of the womb making people laugh. In his 20’s he tried a few …

$40 – $65
9:30 pm - 11:00 pm Event Series

Anthony Rodia

March 31 @ 9:30 pm - 11:00 pm Event Series

Anthony Rodia

A first-generation Italian-American born and raised right here in Westchester County, New York, Anthony Rodia came out of the womb making people laugh. In his 20’s he tried a few …

$40 – $65
9:30 am - 4:00 pm Event Series

Lyndhurst Tours

April 1 @ 9:30 am - 4:00 pm Event Series

Lyndhurst Tours

Lyndhurst, one of America’s finest Gothic Revival mansions, overlooks the Hudson River in Tarrytown, NY. The estate was shaped for more than a century by three families and their staff: The …

$18 – $42
8:00 pm - 9:30 pm

The Manhattan Transfer 50th Anniversary

April 1 @ 8:00 pm - 9:30 pm

The Manhattan Transfer 50th Anniversary

The 10-time Grammy-winning vocal group, The Manhattan Transfer, is celebrating 50 years of their distinctive and eclectic sound with what they are calling their “final world tour.” Founded in 1972 …

$55 – $85
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  • Warner Library Fall Book Sale

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