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    • Headless Horseman Statue
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    • Octagon House
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      • Rocky’s 5K
    • Sleepy Hollow Cemetery
    • Sleepy Hollow Lighthouse
    • Sunnyside
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  • 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
Three pumpkins nestled in fallen leaves in Sleepy Hollow Cemetery.

Tarrytown Halloween Parade

Tarrytown Halloween Parade and block party in full swing on Main Street.The 20th annual Village of Tarrytown Halloween Parade steps off from Patriot’s Park at 5:30pm on Saturday, October 29. The parade route runs south along Broadway to Tarrytown’s Main Street. Block party to follow on Main Street with a DJ and live music, outdoor dining, performers, and much more!

The Halloween parade is festive and fun for the whole family. Viewing along the the parade route is free and you can also participate by marching with a theme as a group or float for a chance to win prizes! Registration is required to be eligible for prizes.

Fun fact: the starting point of the Tarrytown Halloween Parade is Patriots Park, which was the historic location of Wiley’s Swamp in “The Legend of Sleepy Hollow” where Ichabod Crane first spots the Headless Horseman.

In the dark shadow of the grove, on the margin of the brook, [Ichabod] beheld something huge, misshapen and towering. It stirred not, but seemed gathered up in the gloom, like some gigantic monster ready to spring upon the traveler. . . He appeared to be a horseman of large dimensions, and mounted on a black horse of powerful frame. -The Legend of Sleepy Hollow

Where: Patriots Park, Route 9, Tarrytown, NY 10591

2022 date: October 29th, 5:30pm. Rain date October 30th.

For information: Village of Tarrytown Recreation Department, 914-631-8347, https://www.tarrytownhalloweenparade.com


Tarrytown Halloween Parade

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Category: 2022 Events

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10:00 am
Washington Irving's home, Sunnyside, is framed by a clear, blue sky and the white gravel driveway.
May 15 @ 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 15 @ 10:00 am - 5:00 pm Recurring

Octagon House Tours

Armour-Stiner Octagon House 45 W Clinton Avenue, Irvington
$27 – $29
May 15 @ 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 15 @ 11:30 am - 12:30 pm Recurring

The Original Knickerbocker Tour

Sleepy Hollow Cemetery - South Gate 430 North Broadway, Sleepy Hollow
$15
12:00 pm
A view of the front entrance to Union Church of Pocantico Hills against a deep blue sky.
May 15 @ 12:00 pm - 3:00 pm Recurring

Union Church Tours

Union Church of Pocantico Hills 555 Bedford Road, Sleepy Hollow
$9
+ 6 More
10:00 am
The Octagon House in Irvington, NY is open seasonally for tours.
May 16 @ 10:00 am - 5:00 pm Recurring

Octagon House Tours

Armour-Stiner Octagon House 45 W Clinton Avenue, Irvington
$27 – $29
  • No events scheduled for May 17, 2022.
  • No events scheduled for May 18, 2022.
10:00 am
The Octagon House in Irvington, NY is open seasonally for tours.
May 19 @ 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.
May 19 @ 4:30 pm - 6:30 pm Recurring

Old Croton Aqueduct Weir Tour

Joseph G. Caputo Community Center 95 Broadway, Ossining
Free
10:00 am
Washington Irving's home, Sunnyside, is framed by a clear, blue sky and the white gravel driveway.
May 20 @ 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 20 @ 10:00 am - 5:00 pm Recurring

Octagon House Tours

Armour-Stiner Octagon House 45 W Clinton Avenue, Irvington
$27 – $29
May 20 @ 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 20 @ 10:30 am - 3:30 pm Recurring

Union Church Tours

Union Church of Pocantico Hills 555 Bedford Road, Sleepy Hollow
$9
7:00 pm
Jazz musician Houston Person poses with his saxophone.
May 20 @ 7:00 pm - 8:30 pm Recurring

Houston Person Quartet

Jazz Forum Club 1 Dixon Lane, Tarrytown
$30 – $35
8:00 pm
Promotional image of Dar Williams and Sophie B. Hawkins for their Tarrytown Music Hall performance.
May 20 @ 8:00 pm - 9:30 pm

Dar Williams with Special Guest Sophie B Hawkins

Tarrytown Music Hall 13 Main Street, Tarrytown
$35 – $45
+ 4 More
10:00 am
Washington Irving's home, Sunnyside, is framed by a clear, blue sky and the white gravel driveway.
May 21 @ 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 21 @ 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 21 @ 10:00 am - 5:00 pm Recurring

Kykuit Tours

Philipsburg Manor 381 North Broadway, Sleepy Hollow
$18 – $60
May 21 @ 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 21 @ 10:30 am - 3:30 pm Recurring

Union Church Tours

Union Church of Pocantico Hills 555 Bedford Road, Sleepy Hollow
$9
11:00 am
A Sleepy Hollow Cemetery walking tour pauses at the gate to Washington Irving's family lot.
May 21 @ 11:30 am - 12:30 pm Recurring

The Original Knickerbocker Tour

Sleepy Hollow Cemetery - South Gate 430 North Broadway, Sleepy Hollow
$15
2:00 pm
A Sleepy Hollow Cemetery walking tour pauses at the gate to Washington Irving's family lot.
May 21 @ 2:00 pm - 3:00 pm Recurring

The Original Knickerbocker Tour

Sleepy Hollow Cemetery - South Gate 430 North Broadway, Sleepy Hollow
$15
+ 8 More

Week of Events

Sun 15

Mon 16

Tue 17

Wed 18

Thu 19

Fri 20

Sat 21

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 15 @ 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 15 @ 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
10:30 am - 3:30 pm Recurring

Philipsburg Manor Tours

May 15 @ 10:30 am - 3:30 pm Recurring

Philipsburg Manor Tours

Journey to Colonial America! Wander along a woodland path and enter the year 1750, when Philipsburg Manor was a thriving milling and trading complex that was home to several hundred tenant …

$12 – $17
+ 6 More
10:00 am - 5:00 pm Recurring

Octagon House Tours

The Octagon House in Irvington, NY is open seasonally for tours.
May 16 @ 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
10:00 am - 5:00 pm Recurring

Octagon House Tours

The Octagon House in Irvington, NY is open seasonally for tours.
May 19 @ 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.
May 19 @ 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
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 20 @ 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 20 @ 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
10:30 am - 3:30 pm Recurring

Philipsburg Manor Tours

May 20 @ 10:30 am - 3:30 pm Recurring

Philipsburg Manor Tours

Journey to Colonial America! Wander along a woodland path and enter the year 1750, when Philipsburg Manor was a thriving milling and trading complex that was home to several hundred tenant …

$12 – $17
+ 4 More
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 21 @ 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 21 @ 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
10:00 am - 5:00 pm Recurring

Kykuit Tours

A view of the main entranct to Kykuit, the John D. Rockefeller mansion.
May 21 @ 10:00 am - 5:00 pm Recurring

Kykuit Tours

Built between 1906 and 1913, Kykuit was home to four generations of the Rockefeller family. In 2022 the site will be open for guided tours Saturday-Sunday from May 21-October 2; …

$18 – $60
+ 8 More
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