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Visit Sleepy Hollow

Where the Legend Lives

  • See
    • Christ Episcopal Church
    • Headless Horseman Bridge
    • Headless Horseman Statue
    • Historical Society
    • Kykuit
    • Legend Landmarks
    • Lyndhurst
      • Sunset Jazz at Lyndhurst Summer Series
    • 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
    • Jazz at Horan’s Landing Park
    • Jazz at Pierson Park
    • Sleepy Hollow Cemetery Tours
    • 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
    • Directions
  • See
    • Christ Episcopal Church
    • Headless Horseman Bridge
    • Headless Horseman Statue
    • Historical Society
    • Kykuit
    • Legend Landmarks
    • Lyndhurst
      • Sunset Jazz at Lyndhurst Summer Series
    • 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
    • Jazz at Horan’s Landing Park
    • Jazz at Pierson Park
    • Sleepy Hollow Cemetery Tours
    • 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
    • Directions

Historical Society Tours

The main entrance to the historical society, showing the ornate iron railing around the property.

Tour 1: Tarryhollow: Irving, the Old Dutch Church and the Colonial Experience

Travel with back in time to when the first Dutch families settled in this area. Hear the history of the Philipse family and Philipsburg Manor, one of the largest colonial estates in the Hudson River Valley. On this 1 hour 30 minute walking tour you will learn about Frederick Philipse’s Upper Mills and then visit the historic Old Dutch Church, made famous by Washington Irving’s Legend of Sleepy Hollow.  Following that you will spend time in the surrounding burying ground visiting the people who lived in the Neutral Ground and fought in the American Revolution, many of whom inspired Irving’s characters in his tales….

2022 Dates: Tours will be held 1-3 times a day on weekends between September 11 and November 6, 2022.

Where: Tour starts at 418 North Broadway/11 Dell Street, Sleepy Hollow, New York. Limited parking is available in the neighborhood (please do not park on the grounds of Sleepy Hollow Cemetery).

Tickets: https://www.thehistoricalsociety.net/events/tours-tarryhollow/


Tour 2: Tarryhollow: Heroes and Villains of the Hollow

Although small in size, the villages of Tarrytown and Sleepy Hollow have been home to larger than life personalities and events that shaped American history. On this two-hour walking tour, you will visit the Captors’ Monument and learn about the three local militiamen who captured British spy Major John André, triggering the discovery of Benedict Arnold’s treason. You will hear about the men and women of the Philipse family, some of the largest landholders in colonial New York, who lost everything by backing the wrong side in the American Revolution. You will ponder a murder mystery immortalized by one of America’s most famous authors that still intrigues investigators today.  Heroes and happenstance, traitors and treason – all awaiting your discovery in one history-packed square mile.

2022 Dates: Sunday, September 11, 2022 at 12:30 pm
. Saturday, October 8, 2022 at 3:00 pm
. Sunday, October 16, 2022 at 12:30 pm.

Where: Tour starts at Patriots Park, near the Captors Monument

Information: historicalsociety10591@gmail.com


Tour 3: Tarryhollow: Walking Through Time

A historical walking tour that explores the many layers of our wonderful community.

This two-hour tour will introduce you to the unique history of Tarrytown and Sleepy Hollow and to some of the most intriguing people who have ever lived here. The guides will lead you through the many sections of our historic Hudson River villages and regale you with enticing tales of local lore. Starting from Patriots Park, you will journey into the heart of Tarrytown, walking past historic sites and buildings while the guide shares stories of the individuals who made these places their home. The tales include historical accounts of real people and events, as well as a few unexplained incidents from the area’s legendary past. Each of our past residents has left their mark on the community, and a few of them may still linger nearby!

2022 Dates: Saturday September 10 at 10:00 am. Sunday October 30 at 10:00 am.

Where: Tour starts at Patriots Park, near the Captors Monument

Information: historicalsociety10591@gmail.com

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Events Calendar

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  • Week of June 4
  • Previous week
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7:00 am
June 4 @ 7:00 am - 9:00 am Event Series

Small Group Birding at Lyndhurst

Lyndhurst 635 South Broadway, Tarrytown
Free
9:00 am
June 4 @ 9:30 am - 4:00 pm Event Series

Lyndhurst Tours

Lyndhurst 635 South Broadway, Tarrytown
$18 – $42
10:00 am
The Octagon House in Irvington, NY is open seasonally for tours.
June 4 @ 10:00 am - 5:00 pm Event Series

Victorian Springtime at The Octagon House

Armour-Stiner Octagon House 45 W Clinton Avenue, Irvington
$29
A view of the 2022 Tarrytown Street fair showing vendor tents outside the Music Hall.
June 4 @ 10:00 am - 4:00 pm

Tarrytown Street Fair

Main Street, Tarrytown Main Street, Tarrytown
Free
+ 4 More
9:00 am
June 5 @ 9:30 am - 4:00 pm Event Series

Lyndhurst Tours

Lyndhurst 635 South Broadway, Tarrytown
$18 – $42
10:00 am
The Octagon House in Irvington, NY is open seasonally for tours.
June 5 @ 10:00 am - 5:00 pm Event Series

Victorian Springtime at The Octagon House

Armour-Stiner Octagon House 45 W Clinton Avenue, Irvington
$29
  • No events scheduled for June 6, 2023.
  • No events scheduled for June 7, 2023.
9:00 am
June 8 @ 9:30 am - 4:00 pm Event Series

Lyndhurst Tours

Lyndhurst 635 South Broadway, Tarrytown
$18 – $42
10:00 am
The Octagon House in Irvington, NY is open seasonally for tours.
June 8 @ 10:00 am - 5:00 pm Event Series

Victorian Springtime at The Octagon House

Armour-Stiner Octagon House 45 W Clinton Avenue, Irvington
$29
9:00 am
June 9 @ 9:30 am - 4:00 pm Event Series

Lyndhurst Tours

Lyndhurst 635 South Broadway, Tarrytown
$18 – $42
10:00 am
The Octagon House in Irvington, NY is open seasonally for tours.
June 9 @ 10:00 am - 5:00 pm Event Series

Victorian Springtime at The Octagon House

Armour-Stiner Octagon House 45 W Clinton Avenue, Irvington
$29
9:00 am
June 10 @ 9:30 am - 4:00 pm Event Series

Lyndhurst Tours

Lyndhurst 635 South Broadway, Tarrytown
$18 – $42
10:00 am
The Octagon House in Irvington, NY is open seasonally for tours.
June 10 @ 10:00 am - 5:00 pm Event Series

Victorian Springtime at The Octagon House

Armour-Stiner Octagon House 45 W Clinton Avenue, Irvington
$29
11:00 am
A Sleepy Hollow Cemetery walking tour pauses at the gate to Washington Irving's family lot.
June 10 @ 11:00 am - 12:00 pm Event Series

The Original Knickerbocker Tour

Sleepy Hollow Cemetery - South Gate 430 North Broadway, Sleepy Hollow
$15
+ 4 More

Week of Events

Sun 4

Mon 5

Tue 6

Wed 7

Thu 8

Fri 9

Sat 10

7:00 am - 9:00 am Event Series

Small Group Birding at Lyndhurst

June 4 @ 7:00 am - 9:00 am Event Series

Small Group Birding at Lyndhurst

Small group birding at Lyndhurst, the Jay Gould mansion in Tarrytown, a partnership between Lyndhurst Mansion and Saw Mill River Audubon. These beautiful grounds along the Hudson River are likely to …

Free
9:30 am - 4:00 pm Event Series

Lyndhurst Tours

June 4 @ 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
10:00 am - 5:00 pm Event Series

Victorian Springtime at The Octagon House

The Octagon House in Irvington, NY is open seasonally for tours.
June 4 @ 10:00 am - 5:00 pm Event Series

Victorian Springtime at The Octagon House

Experience this whimsical 1872 Summer home and its marvelously intact, 19th-century landscape during the most delightful time of the year! The tour will include a brief history of specimen plants …

$29
+ 4 More
9:30 am - 4:00 pm Event Series

Lyndhurst Tours

June 5 @ 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
10:00 am - 5:00 pm Event Series

Victorian Springtime at The Octagon House

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

Victorian Springtime at The Octagon House

Experience this whimsical 1872 Summer home and its marvelously intact, 19th-century landscape during the most delightful time of the year! The tour will include a brief history of specimen plants …

$29
9:30 am - 4:00 pm Event Series

Lyndhurst Tours

June 8 @ 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
10:00 am - 5:00 pm Event Series

Victorian Springtime at The Octagon House

The Octagon House in Irvington, NY is open seasonally for tours.
June 8 @ 10:00 am - 5:00 pm Event Series

Victorian Springtime at The Octagon House

Experience this whimsical 1872 Summer home and its marvelously intact, 19th-century landscape during the most delightful time of the year! The tour will include a brief history of specimen plants …

$29
9:30 am - 4:00 pm Event Series

Lyndhurst Tours

June 9 @ 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
10:00 am - 5:00 pm Event Series

Victorian Springtime at The Octagon House

The Octagon House in Irvington, NY is open seasonally for tours.
June 9 @ 10:00 am - 5:00 pm Event Series

Victorian Springtime at The Octagon House

Experience this whimsical 1872 Summer home and its marvelously intact, 19th-century landscape during the most delightful time of the year! The tour will include a brief history of specimen plants …

$29
9:30 am - 4:00 pm Event Series

Lyndhurst Tours

June 10 @ 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
10:00 am - 5:00 pm Event Series

Victorian Springtime at The Octagon House

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

Victorian Springtime at The Octagon House

Experience this whimsical 1872 Summer home and its marvelously intact, 19th-century landscape during the most delightful time of the year! The tour will include a brief history of specimen plants …

$29
11:00 am - 12:00 pm Event Series

The Original Knickerbocker Tour

A Sleepy Hollow Cemetery walking tour pauses at the gate to Washington Irving's family lot.
June 10 @ 11:00 am - 12:00 pm Event Series

The Original Knickerbocker Tour

The Original Knickerbocker: Washington Irving & “The Legend of Sleepy Hollow”. Meet the father of the American short story on this one-hour tour of Sleepy Hollow Cemetery! Learn all about …

$15
+ 4 More
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  • Victorian Christmas at the Octagon House

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