Recurring Event The Original Knickerbocker Tour

The Original Knickerbocker Tour

Sleepy Hollow Cemetery - South Gate 430 North Broadway, Sleepy Hollow, NY

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 Washington Irving, his impact on American Literature and the enduring appeal of "The Legend of Sleepy Hollow", which recently celebrated its Bicentennial. Best of all, …

$15

The Legends of The Legend of Sleepy Hollow

Christ Church San Marcos 43 South Broadway, Tarrytown, NY

Hear Master Storyteller Jonathan Kruk spin the haunting tales of the ghost surrounding the Headless Horseman and the galloping goblin's origin story! Tarrytown and Sleepy Hollow have long hosted several famed spirits: Tragic Major Andre the spy who conspired with the traitorous Benedict Arnold, The Wailing Woman in White, Ship-sinking Imps on the Hudson River, Hulda the …

$20

The Legend – Cirque Theatre Performance

East Parcel 60 Continental Street, Sleepy Hollow, NY

Step back in time. It’s the 1800’s. Hear the clamoring metal horseshoes click across cobblestone roads in this dark Sleepy Hollow tale. The LEGEND is a simmering adaptation of Washington Irving’s iconic ghost story, “The Legend of Sleepy Hollow.” Audiences will be treated to a cirque/theatre noir production with narration by Washington Irving himself – …

$30
Recurring Event Classic Daytime Cemetery Tour

Classic Daytime Cemetery Tour

Sleepy Hollow Cemetery - South Gate 430 North Broadway, Sleepy Hollow, NY

Soak up the beauty of this 173-year old cemetery while your guide regales you with stories of the fascinating people resting here in peace. This two-hour daytime walk is the perfect way "to have a colloquy among the tombs" as Washington Irving, famous author of "The Legend of Sleepy Hollow", did himself back in 1849. You'll …

$25
Recurring Event Musical: Hearts of the Hollow

Musical: Hearts of the Hollow

The Whipple Feeley Chapel 200 Gipsy Trail Road, Carmel, NY

You think know The Legend . . . come see new twists and turns in Hearts of the Hollow! An exciting new musical inspired by Washington Irving's classic short story "The Legend of Sleepy Hollow", this special seasonal event will delight audiences with 20 original songs and a story where suspense, adventure, and romance come …

$29 – $49
Recurring Event The Great Jack O’Lantern Blaze

The Great Jack O’Lantern Blaze

Van Cortlandt Manor 525 S Riverside Avenue, Croton-on-Hudson, NY

The Great Jack O'Lantern Blaze is the Hudson Valley’s most electrifying fall happening! Meander through the 18th-century landscape of Van Cortlandt Manor and discover a breathtaking display of more than 7,000 illuminated jack o’ lanterns—all designed and hand-carved on site by a team of talented artisans. New for 2022, watch the animated “Jack” Smith Shop …

$24 – $99

The Legend – Cirque Theatre Performance

East Parcel 60 Continental Street, Sleepy Hollow, NY

Step back in time. It’s the 1800’s. Hear the clamoring metal horseshoes click across cobblestone roads in this dark Sleepy Hollow tale. The LEGEND is a simmering adaptation of Washington Irving’s iconic ghost story, “The Legend of Sleepy Hollow.” Audiences will be treated to a cirque/theatre noir production with narration by Washington Irving himself – …

$30
Recurring Event Octagon House Classic Tour

Octagon House Classic Tour

Armour-Stiner Octagon House 45 W Clinton Avenue, Irvington, NY

The Armour-Stiner Octagon House, a registered National Historic Landmark, was created as a summer retreat by tea-importer Joseph Stiner. Its shape was based on the theories of Orson Squire Fowler, a phrenologist, who believed octagonal houses enclosed more space, allowed the sun in at all times, and permitted more views into the landscape. The tour …

$29

Women’s Work Art Tour – Lyndhurst

Lyndhurst 635 South Broadway, Tarrytown, NY

Women’s Work exhibition at the Lyndhurst mansion in Tarrytown tracks the deep, pervasive, and continuing influence of the domestic craft tradition in the practice of contemporary women artists. The exhibition explores how this embrace of feminine domesticity as an expression of gender-specific artistic identity was a constant practice for the growing number of women artists who …

$16 – $30

Octagon House Myths and Mysteries Tour

Armour-Stiner Octagon House 45 W Clinton Avenue, Irvington, NY

18 miles north of New York City, high on a bank along The Hudson River sits The Armour-Stiner (Octagon) House. Built in 1860, this enigmatic, eight-sided, domed landmark is the pride of the Village of Irvington, in the heart of “Sleepy Hollow Country.” During the month of October, The Octagon House is pleased to announce …

$29

Octagon House Myths and Mysteries Tour

Armour-Stiner Octagon House 45 W Clinton Avenue, Irvington, NY

18 miles north of New York City, high on a bank along The Hudson River sits The Armour-Stiner (Octagon) House. Built in 1860, this enigmatic, eight-sided, domed landmark is the pride of the Village of Irvington, in the heart of “Sleepy Hollow Country.” During the month of October, The Octagon House is pleased to announce …

$29

There’s something for everyone in the real Sleepy Hollow—farmers markets, live music, street fairs, historic homes, hiking trails, kayaking and boating on the Hudson River. Halloween season brings even more for the whole family—haunted hayrides, blazing pumpkins, costumed 5K run, Halloween parade, and of course, the Headless Horseman! For the latest on Fall events, visit our guide to Halloween in Sleepy Hollow.