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Octagon House Tours

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

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
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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 …

Free
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Sunnyside Tours

Sunnyside 3 W Sunnyside Lane, Irvington, NY

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
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Octagon House Tours

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

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
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Philipsburg Manor Tours

Philipsburg Manor 381 North Broadway, Sleepy Hollow, NY

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
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Union Church Tours

Union Church of Pocantico Hills 555 Bedford Road, Sleepy Hollow, NY

The Union Church of Pocantico Hills is a repository of awe-inspiring art by Matisse & Chagall. Stained-glass windows by European masters, commissioned by the Rockefeller family, adorn this unassuming country …

$9
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Houston Person Quartet

Jazz Forum Club 1 Dixon Lane, Tarrytown, NY

Nothing, it seems, stops Houston Person, the reigning King of the Boss Tenor who is now in his sixth decade of performing. His new record (he’s released over 85 of …

$30 – $35

Dar Williams with Special Guest Sophie B Hawkins

Tarrytown Music Hall 13 Main Street, Tarrytown, NY

Dar Williams’ lyrics contain bouquets of optimism, delivered on melodies alternating between beguiling lightness and understated gravity. Williams strongly believes that all of us possess our own power and ability …

$35 – $45
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Houston Person Quartet

Jazz Forum Club 1 Dixon Lane, Tarrytown, NY

Nothing, it seems, stops Houston Person, the reigning King of the Boss Tenor who is now in his sixth decade of performing. His new record (he’s released over 85 of …

$30 – $35
Recurring

Sunnyside Tours

Sunnyside 3 W Sunnyside Lane, Irvington, NY

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
Recurring

Octagon House Tours

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

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
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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; …

$18 – $60

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.