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
Recurring Event Kykuit Tours

Kykuit Tours

Philipsburg Manor 381 North Broadway, Sleepy Hollow, NY

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; and Wednesday-Monday between October 5-November 13. There are three distinct Kykuit tours available: Classic Tour: Great for first-time visitors. Your visit will include the main floor of …

$18 – $60

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

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 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

Old Croton Aqueduct Weir Tour

Joseph G. Caputo Community Center 95 Broadway, Ossining, NY

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 is a horseshoe-shaped brick tunnel 8.5 feet high by 7.5 feet wide, set on a stone foundation and protected with an earthen cover and stone …

Free

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

Murder and Mayhem Walking Tour

Sleepy Hollow Cemetery - North Gate 540 North Broadway, Sleepy Hollow, NY

The true stories on this two-hour lantern tour are so grim, you just might have nightmares! Curious to learn about a family that lost 5 children one terrible afternoon, or a horrific murder that led police on a multi-state chase? Maybe you’d like to hear about a son who shot his father before turning the …

$45

American Aristocrats Cemetery Tour

Sleepy Hollow Cemetery - North Gate 540 North Broadway, Sleepy Hollow, NY

Short on time? Make the most of it and meet the crème de la crème on this one-hour lantern tour of Sleepy Hollow Cemetery! The Gilded Age began after the Civil War and ended around 1900. It was a time of tremendous industrialization and rapid economic growth. Railroads were built to connect the East Coast …

$30

The Orchestra – Starring Former Members of Electric Light Orchestra

Tarrytown Music Hall 13 Main Street, Tarrytown, NY

The Orchestra Starring Former Members of Electric Light Orchestra performs all of the Original ELO greatest hits as certified by the Billboard Top 40 Category in the United States as well as the songs which charted by the New Musical Express and the Record Retailers Music Week charts in the United Kingdom music press, from …

$49 – $79
Recurring Event Home of the ‘Legend’

Home of the ‘Legend’

Sunnyside 3 W Sunnyside Lane, Irvington, NY

At this family-friendly happening, visitors can tour Washington Irving’s house—decorated for the season—watch an original shadow puppet short film, and enjoy games on the lawn. A special exhibit highlights how "The Legend of Sleepy Hollow" has lived in the imagination of popular culture through the centuries since its publication.

Free – $12
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

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.