• Menu
  • Skip to right header navigation
  • Skip to main content
  • Skip to primary sidebar

Before Header

Visit Sleepy Hollow

Where the Legend Lives

  • 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 
      • Rocky’s 5K
    • Sleepy Hollow Cemetery
    • Sleepy Hollow Lighthouse
    • Sunnyside
    • Union Church of Pocantico Hills
  • Events
    • Events Calendar
    • Jazz Forum
    • Jazz at Horan’s Landing Park
    • Jazz at Pierson Park
    • Sleepy Hollow Cemetery Tours
    • Sunset Jazz at Lyndhurst Summer Series
    • Tarrytown Music Hall Performances
    • Halloween in Sleepy Hollow
  • 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
    • Directions
    • Carl’s Mill
    • Movies Made Here
    • Spook Rock
    • Florence Inn
  • 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 
      • Rocky’s 5K
    • Sleepy Hollow Cemetery
    • Sleepy Hollow Lighthouse
    • Sunnyside
    • Union Church of Pocantico Hills
  • Events
    • Events Calendar
    • Jazz Forum
    • Jazz at Horan’s Landing Park
    • Jazz at Pierson Park
    • Sleepy Hollow Cemetery Tours
    • Sunset Jazz at Lyndhurst Summer Series
    • Tarrytown Music Hall Performances
    • Halloween in Sleepy Hollow
  • 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
    • Directions
    • Carl’s Mill
    • Movies Made Here
    • Spook Rock
    • Florence Inn
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 5 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: « Hulda’s Night at Rockefeller State Park Preserve
Next Post: Rocky’s 5K A runner on the Ash Tree Loop trail of Rockefeller State Park Preserve practices for Rocky’s 5K.»

Primary Sidebar

Advertisement for Sleepy Hollow Cemetery day and evening walking tours.

Recent Posts

  • Spring Makers Market
  • Rocky’s 5K
  • Sleepy Hollow Street Fair
  • Hulda’s Night at Rockefeller State Park Preserve
  • Tarrytown Halloween Parade
Save on your hotel - hotelscombined.com

Loading view.
  • Week of May 29
  • Previous week
  • Next week
9:00 am
A promotional image for Lyndhurst Ramble Tour shows apple trees silhouetted against a sunny lawn.
May 29 @ 9:30 am - 11:00 am Recurring

History in the Landscape Tour – Lyndhurst

Lyndhurst 635 South Broadway, Tarrytown
$15 – $20
10:00 am
Washington Irving's home, Sunnyside, is framed by a clear, blue sky and the white gravel driveway.
May 29 @ 10:00 am - 3:30 pm Recurring

Sunnyside Tours

Sunnyside 3 W Sunnyside Lane, Irvington
$12 – $17
The Octagon House in Irvington, NY is open seasonally for tours.
May 29 @ 10:00 am - 5:00 pm Recurring

Octagon House Tours

Armour-Stiner Octagon House 45 W Clinton Avenue, Irvington
$27 – $29
A view of the main entranct to Kykuit, the John D. Rockefeller mansion.
May 29 @ 10:00 am - 5:00 pm Recurring

Kykuit Tours

Philipsburg Manor 381 North Broadway, Sleepy Hollow
$18 – $60
May 29 @ 10:30 am - 12:00 pm Recurring

Women’s Work Art Tour – Lyndhurst

Lyndhurst 635 South Broadway, Tarrytown
$16 – $30
May 29 @ 10:30 am - 3:30 pm Recurring

Philipsburg Manor Tours

Philipsburg Manor 381 North Broadway, Sleepy Hollow
$12 – $17
11:00 am
A Sleepy Hollow Cemetery walking tour pauses at the gate to Washington Irving's family lot.
May 29 @ 11:30 am - 12:30 pm Recurring

The Original Knickerbocker Tour

Sleepy Hollow Cemetery - South Gate 430 North Broadway, Sleepy Hollow
$15
+ 8 More
9:00 am
Blue sky reflects off a stream at Rockefeller State Park Preserve.
May 30 @ 9:30 am - 11:00 am Recurring

Tree Identification Walk

Rockefeller State Park Preserve 125 Phelps Way, Pleasantville
$3
10:00 am
Washington Irving's home, Sunnyside, is framed by a clear, blue sky and the white gravel driveway.
May 30 @ 10:00 am - 3:30 pm Recurring

Sunnyside Tours

Sunnyside 3 W Sunnyside Lane, Irvington
$12 – $17
The Octagon House in Irvington, NY is open seasonally for tours.
May 30 @ 10:00 am - 5:00 pm Recurring

Octagon House Tours

Armour-Stiner Octagon House 45 W Clinton Avenue, Irvington
$27 – $29
May 30 @ 10:30 am - 12:00 pm Recurring

Women’s Work Art Tour – Lyndhurst

Lyndhurst 635 South Broadway, Tarrytown
$16 – $30
May 30 @ 10:30 am - 3:30 pm Recurring

Philipsburg Manor Tours

Philipsburg Manor 381 North Broadway, Sleepy Hollow
$12 – $17
A view of the front entrance to Union Church of Pocantico Hills against a deep blue sky.
May 30 @ 10:30 am - 3:30 pm Recurring

Union Church Tours

Union Church of Pocantico Hills 555 Bedford Road, Sleepy Hollow
$9
+ 3 More
  • No events scheduled for May 31, 2022.
  • No events scheduled for June 1, 2022.
10:00 am
The Octagon House in Irvington, NY is open seasonally for tours.
June 2 @ 10:00 am - 5:00 pm Recurring

Octagon House Tours

Armour-Stiner Octagon House 45 W Clinton Avenue, Irvington
$27 – $29
4:00 pm
Interior of the Old Croton Aqueduct waste water weir at Ossining, New York.
June 2 @ 4:30 pm - 6:30 pm Recurring

Old Croton Aqueduct Weir Tour

Joseph G. Caputo Community Center 95 Broadway, Ossining
Free
6:00 pm
June 2 @ 6:30 pm - 9:00 pm

Lyndhurst Spring Gala

Lyndhurst 635 South Broadway, Tarrytown
$175 – $500
9:00 am
A promotional image for Lyndhurst Ramble Tour shows apple trees silhouetted against a sunny lawn.
June 3 @ 9:30 am - 11:00 am Recurring

History in the Landscape Tour – Lyndhurst

Lyndhurst 635 South Broadway, Tarrytown
$15 – $20
10:00 am
Washington Irving's home, Sunnyside, is framed by a clear, blue sky and the white gravel driveway.
June 3 @ 10:00 am - 3:30 pm Recurring

Sunnyside Tours

Sunnyside 3 W Sunnyside Lane, Irvington
$12 – $17
The Octagon House in Irvington, NY is open seasonally for tours.
June 3 @ 10:00 am - 5:00 pm Recurring

Octagon House Tours

Armour-Stiner Octagon House 45 W Clinton Avenue, Irvington
$27 – $29
June 3 @ 10:30 am - 12:00 pm Recurring

Women’s Work Art Tour – Lyndhurst

Lyndhurst 635 South Broadway, Tarrytown
$16 – $30
June 3 @ 10:30 am - 3:30 pm Recurring

Philipsburg Manor Tours

Philipsburg Manor 381 North Broadway, Sleepy Hollow
$12 – $17
A view of the front entrance to Union Church of Pocantico Hills against a deep blue sky.
June 3 @ 10:30 am - 3:30 pm Recurring

Union Church Tours

Union Church of Pocantico Hills 555 Bedford Road, Sleepy Hollow
$9
7:00 pm
The Bill Charlap jazz trio poses for a photograph.
June 3 @ 7:00 pm - 8:30 pm Recurring

Bill Charlap Trio featuring Peter Washington & Kenny Washington

Jazz Forum Club 1 Dixon Lane, Tarrytown
$30 – $35
+ 5 More
8:00 am
Fresh produce from Berry Brook Farm at Tarrytown and Sleepy Hollow Farmers Market.
June 4 @ 8:30 am - 2:00 pm Recurring

TaSH Farmers Market

Patriots Park Patriots Park, Tarrytown
Free
9:00 am
Runners on the trails at Rockwood Hall 10k race.
June 4 @ 9:00 am - 11:00 am

Rockwood Ramble 10k

Rockwood Hall 1 Rockwood Road, Sleepy Hollow
$20 – $50
A promotional image for Lyndhurst Ramble Tour shows apple trees silhouetted against a sunny lawn.
June 4 @ 9:30 am - 11:00 am Recurring

History in the Landscape Tour – Lyndhurst

Lyndhurst 635 South Broadway, Tarrytown
$15 – $20
10:00 am
Washington Irving's home, Sunnyside, is framed by a clear, blue sky and the white gravel driveway.
June 4 @ 10:00 am - 3:30 pm Recurring

Sunnyside Tours

Sunnyside 3 W Sunnyside Lane, Irvington
$12 – $17
The Octagon House in Irvington, NY is open seasonally for tours.
June 4 @ 10:00 am - 5:00 pm Recurring

Octagon House Tours

Armour-Stiner Octagon House 45 W Clinton Avenue, Irvington
$27 – $29
A view of the main entranct to Kykuit, the John D. Rockefeller mansion.
June 4 @ 10:00 am - 5:00 pm Recurring

Kykuit Tours

Philipsburg Manor 381 North Broadway, Sleepy Hollow
$18 – $60
June 4 @ 10:30 am - 12:00 pm Recurring

Women’s Work Art Tour – Lyndhurst

Lyndhurst 635 South Broadway, Tarrytown
$16 – $30
June 4 @ 10:30 am - 3:30 pm Recurring

Philipsburg Manor Tours

Philipsburg Manor 381 North Broadway, Sleepy Hollow
$12 – $17
A view of the front entrance to Union Church of Pocantico Hills against a deep blue sky.
June 4 @ 10:30 am - 3:30 pm Recurring

Union Church Tours

Union Church of Pocantico Hills 555 Bedford Road, Sleepy Hollow
$9
+ 11 More

Week of Events

Sun 29

Mon 30

Tue 31

Wed 1

Thu 2

Fri 3

Sat 4

9:30 am - 11:00 am Recurring

History in the Landscape Tour – Lyndhurst

A promotional image for Lyndhurst Ramble Tour shows apple trees silhouetted against a sunny lawn.
May 29 @ 9:30 am - 11:00 am Recurring

History in the Landscape Tour – Lyndhurst

This outdoor walking tour examines the history of the landscaped Lyndhurst estate throughout three families’ ownership. Visitors are led down from the Lyndhurst Veranda and its marble garden furniture and …

$15 – $20
10:00 am - 3:30 pm Recurring

Sunnyside Tours

Washington Irving's home, Sunnyside, is framed by a clear, blue sky and the white gravel driveway.
May 29 @ 10:00 am - 3:30 pm Recurring

Sunnyside Tours

A charming, romantic Hudson River landscape. America’s “Founding Father of Literature” created a romantic, picturesque estate nestled along the Hudson riverbank. The enchanted landscape of Washington Irving’s much-loved Sunnyside has …

$12 – $17
10:00 am - 5:00 pm Recurring

Octagon House Tours

The Octagon House in Irvington, NY is open seasonally for tours.
May 29 @ 10:00 am - 5:00 pm Recurring

Octagon House Tours

The Armour-Stiner Octagon House, a registered National Historic Landmark, will be offering a series of guided tours; “Springtime at The Octagon House: Historic Home and Landscape Tour” April 28 through …

$27 – $29
+ 8 More
9:30 am - 11:00 am Recurring

Tree Identification Walk

Blue sky reflects off a stream at Rockefeller State Park Preserve.
May 30 @ 9:30 am - 11:00 am Recurring

Tree Identification Walk

Join Rockefeller State Park Preserve's flora steward, Devyani Mishra, on a leisurely stroll to learn more about trees and other plants in the area and how to identify them. The hike will be …

$3
10:00 am - 3:30 pm Recurring

Sunnyside Tours

Washington Irving's home, Sunnyside, is framed by a clear, blue sky and the white gravel driveway.
May 30 @ 10:00 am - 3:30 pm Recurring

Sunnyside Tours

A charming, romantic Hudson River landscape. America’s “Founding Father of Literature” created a romantic, picturesque estate nestled along the Hudson riverbank. The enchanted landscape of Washington Irving’s much-loved Sunnyside has …

$12 – $17
10:00 am - 5:00 pm Recurring

Octagon House Tours

The Octagon House in Irvington, NY is open seasonally for tours.
May 30 @ 10:00 am - 5:00 pm Recurring

Octagon House Tours

The Armour-Stiner Octagon House, a registered National Historic Landmark, will be offering a series of guided tours; “Springtime at The Octagon House: Historic Home and Landscape Tour” April 28 through …

$27 – $29
+ 3 More
10:00 am - 5:00 pm Recurring

Octagon House Tours

The Octagon House in Irvington, NY is open seasonally for tours.
June 2 @ 10:00 am - 5:00 pm Recurring

Octagon House Tours

The Armour-Stiner Octagon House, a registered National Historic Landmark, will be offering a series of guided tours; “Springtime at The Octagon House: Historic Home and Landscape Tour” April 28 through …

$27 – $29
4:30 pm - 6:30 pm Recurring

Old Croton Aqueduct Weir Tour

Interior of the Old Croton Aqueduct waste water weir at Ossining, New York.
June 2 @ 4:30 pm - 6:30 pm Recurring

Old Croton Aqueduct Weir Tour

The Old Croton Aqueduct, New York City's original water supply, runs from, Croton-on-Hudson into the Bronx and Manhattan, passing through Sleepy Hollow and Tarrytown. For most of its length, the Aqueduct …

Free
6:30 pm - 9:00 pm

Lyndhurst Spring Gala

June 2 @ 6:30 pm - 9:00 pm

Lyndhurst Spring Gala

Celebrating Women’s Work, A New Art Exhibition Enjoy a glorious summer’s evening at the Lyndhurst mansion with an exclusive preview of its acclaimed art exhibit. Thursday, June 2, 2022 6:30 pm Cocktails …

$175 – $500
9:30 am - 11:00 am Recurring

History in the Landscape Tour – Lyndhurst

A promotional image for Lyndhurst Ramble Tour shows apple trees silhouetted against a sunny lawn.
June 3 @ 9:30 am - 11:00 am Recurring

History in the Landscape Tour – Lyndhurst

This outdoor walking tour examines the history of the landscaped Lyndhurst estate throughout three families’ ownership. Visitors are led down from the Lyndhurst Veranda and its marble garden furniture and …

$15 – $20
10:00 am - 3:30 pm Recurring

Sunnyside Tours

Washington Irving's home, Sunnyside, is framed by a clear, blue sky and the white gravel driveway.
June 3 @ 10:00 am - 3:30 pm Recurring

Sunnyside Tours

A charming, romantic Hudson River landscape. America’s “Founding Father of Literature” created a romantic, picturesque estate nestled along the Hudson riverbank. The enchanted landscape of Washington Irving’s much-loved Sunnyside has …

$12 – $17
10:00 am - 5:00 pm Recurring

Octagon House Tours

The Octagon House in Irvington, NY is open seasonally for tours.
June 3 @ 10:00 am - 5:00 pm Recurring

Octagon House Tours

The Armour-Stiner Octagon House, a registered National Historic Landmark, will be offering a series of guided tours; “Springtime at The Octagon House: Historic Home and Landscape Tour” April 28 through …

$27 – $29
+ 5 More
8:30 am - 2:00 pm Recurring

TaSH Farmers Market

Fresh produce from Berry Brook Farm at Tarrytown and Sleepy Hollow Farmers Market.
June 4 @ 8:30 am - 2:00 pm Recurring

TaSH Farmers Market

Fresh Hudson Valley produce, meat, bread, honey, specialty foods, cut flowers, dairy products, beer and wine. There is occasionally live music or demonstrations of traditional crafts. Route 9 (Broadway) next …

Free
9:00 am - 11:00 am

Rockwood Ramble 10k

Runners on the trails at Rockwood Hall 10k race.
June 4 @ 9:00 am - 11:00 am

Rockwood Ramble 10k

Starting and finishing in historic Rockwood Hall, the annual Rockwood Ramble 10K is a favorite. Scenic Hudson River views greet runners before the course veers into the woods. The wide …

$20 – $50
9:30 am - 11:00 am Recurring

History in the Landscape Tour – Lyndhurst

A promotional image for Lyndhurst Ramble Tour shows apple trees silhouetted against a sunny lawn.
June 4 @ 9:30 am - 11:00 am Recurring

History in the Landscape Tour – Lyndhurst

This outdoor walking tour examines the history of the landscaped Lyndhurst estate throughout three families’ ownership. Visitors are led down from the Lyndhurst Veranda and its marble garden furniture and …

$15 – $20
+ 11 More
View Calendar

Copyright © 2022 Sleepy Hollow Cemetery Historic Fund, Inc. · All Rights Reserved · Powered by Mai Theme · Privacy Policy