Sleepy Hollow Street Fair
The Sleepy Hollow Tarrytown Chamber of Commerce’s annual Sleepy Hollow Street Fair takes place this year on Saturday, October 8th, transforming Beekman Avenue into an outdoor market. October is the most exciting …
Free
25 events found.
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Beekman Avenue, Sleepy Hollow Beekman Avenue, Sleepy Hollow, NY, United States
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Home of the ‘Legend’
Sunnyside 3 W Sunnyside Lane, Irvington, NY, United StatesAt 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 …
Free – $12 -
Octagon House Classic Tour
Armour-Stiner Octagon House 45 W Clinton Avenue, Irvington, NY, United StatesThe 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, …
$29 -
Kykuit Tours
Philipsburg Manor 381 North Broadway, Sleepy Hollow, NY, United StatesBuilt 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 -
Philipsburg Manor Tours
Philipsburg Manor 381 North Broadway, Sleepy Hollow, NY, United StatesJourney 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 -
Union Church Tours
Union Church of Pocantico Hills 555 Bedford Road, Sleepy Hollow, NY, United StatesThe 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 -
The Original Knickerbocker Tour
Sleepy Hollow Cemetery South Gate 430 North Broadway, Sleepy Hollow, NY, United StatesThe 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 -
Octagon House Myths and Mysteries Tour
Armour-Stiner Octagon House 45 W Clinton Avenue, Irvington, NY, United States18 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 …
$29 -
The Original Knickerbocker Tour
Sleepy Hollow Cemetery South Gate 430 North Broadway, Sleepy Hollow, NY, United StatesThe 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 -
The Legend – Cirque Theatre Performance
East Parcel 60 Continental Street, Sleepy Hollow, NY, United StatesStep 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 …
$30 -
Classic Daytime Cemetery Tour
Sleepy Hollow Cemetery South Gate 430 North Broadway, Sleepy Hollow, NY, United StatesSoak 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 …
$25 -
Tarryhollow: Heroes and Villains of the Hollow
Patriots Park Patriots Park, Tarrytown, NY, United StatesAlthough 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 …
$24.99 -
The Great Jack O’Lantern Blaze
Van Cortlandt Manor 525 S Riverside Avenue, Croton-on-Hudson, NY, United StatesThe 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 …
$24 – $99 -
Murder and Mayhem Walking Tour
Sleepy Hollow Cemetery North Gate 540 North Broadway, Sleepy Hollow, NY, United StatesThe 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 …
$45 -
Irving’s Legend at Sunnyside
Sunnyside 3 W Sunnyside Lane, Irvington, NY, United StatesIrving’s Legend returns reimagined this fall. Performed under the stars at Washington Irving’s Sunnyside, master storyteller Jonathan Kruk will cast a spell with dramatic performances of the classic tale. Live …
$30 – $70 -
The Legend – Cirque Theatre Performance
East Parcel 60 Continental Street, Sleepy Hollow, NY, United StatesStep 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 …
$30 -
Sleepy Hollow Cemetery Lantern Tour
Sleepy Hollow Cemetery North Gate 540 North Broadway, Sleepy Hollow, NY, United StatesSoak up the history of this famous cemetery by the light of kerosene lanterns! It’s like stepping back in time as you visit some of the most impressive residents, including …
$45 -
American Aristocrats Cemetery Tour
Sleepy Hollow Cemetery North Gate 540 North Broadway, Sleepy Hollow, NY, United StatesShort 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 …
$30 -
Violent Femmes
Tarrytown Music Hall 13 Main Street, Tarrytown, NY, United StatesViolent Femmes formed in 1981 as an acoustic punk band playing on the streets of Milwaukee, Wisconsin. Their main influences at that time were Gene Vincent and the Blue Caps …
$64 – $84 -
American Aristocrats Cemetery Tour
Sleepy Hollow Cemetery North Gate 540 North Broadway, Sleepy Hollow, NY, United StatesShort 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 …
$30 -
Randy Brecker Quintet featuring Ada Rovatti
Jazz Forum Club 1 Dixon Lane, Tarrytown, NY, United StatesJazz trumpeter and composer Randy Brecker has helped shape the sound of jazz, R&B and rock for more than four decades. His trumpet and flugelhorn performances have graced hundreds of …
$30 – $35 -
Murder and Mayhem Walking Tour
Sleepy Hollow Cemetery North Gate 540 North Broadway, Sleepy Hollow, NY, United StatesThe 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 …
$45 -
Sleepy Hollow Cemetery Lantern Tour
Sleepy Hollow Cemetery North Gate 540 North Broadway, Sleepy Hollow, NY, United StatesSoak up the history of this famous cemetery by the light of kerosene lanterns! It’s like stepping back in time as you visit some of the most impressive residents, including …
$45 -
Irvington Farmers Market
Main Street School 101 Main Street, Irvington, NY, United StatesEnjoy live music, river views and a laid-back setting at this small-town Sunday market showcasing the best of what the Hudson Valley has to offer. In season, there is fresh …
Free -
Home of the ‘Legend’
Sunnyside 3 W Sunnyside Lane, Irvington, NY, United StatesAt 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 …
Free – $12
There's something for everyone in Sleepy Hollow Country—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 10K run, Halloween parade, and of course, the Headless Horseman! For the latest on Fall events, visit our guide to Halloween in Sleepy Hollow.