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  • The Legend – Cirque Theatre Performance

    The Legend Cirque
    East Parcel 60 Continental Street, Sleepy Hollow, NY, United States

    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
  • Octagon House Classic Tour

    Octagon House Classic Tour
    Armour-Stiner Octagon House 45 W Clinton Avenue, Irvington, NY, United States

    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
  • Octagon House Myths and Mysteries Tour

    Myths & Mysteries of The Octagon House
    Armour-Stiner Octagon House 45 W Clinton Avenue, Irvington, NY, United States

    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

    Myths & Mysteries of The Octagon House
    Armour-Stiner Octagon House 45 W Clinton Avenue, Irvington, NY, United States

    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

    Myths & Mysteries of The Octagon House
    Armour-Stiner Octagon House 45 W Clinton Avenue, Irvington, NY, United States

    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 Great Jack O’Lantern Blaze

    The Great Jack O’Lantern Blaze
    Van Cortlandt Manor 525 S Riverside Avenue, Croton-on-Hudson, NY, United States

    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
  • Octagon House Classic Tour

    Octagon House Classic Tour
    Armour-Stiner Octagon House 45 W Clinton Avenue, Irvington, NY, United States

    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
  • Octagon House Myths and Mysteries Tour

    Myths & Mysteries of The Octagon House
    Armour-Stiner Octagon House 45 W Clinton Avenue, Irvington, NY, United States

    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
  • Local Lore and Legends

    Local Lore and Legends
    Park Manager Residence 25 Sleepy Hollow Road, Sleepy Hollow, NY, United States

    While Sleepy Hollow is well known for its headless horseman, there are quite a few lesser-known legends that take place on this land. The names of some of our most iconic locations such as Spook Rock, Ravens Rock, Witch’s Spring come from stories that have been told by locals dating back hundreds of years. Join …

    $4
  • The Great Jack O’Lantern Blaze

    The Great Jack O’Lantern Blaze
    Van Cortlandt Manor 525 S Riverside Avenue, Croton-on-Hudson, NY, United States

    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
  • Hudson River Lighthouses with Kevin Woyce

    Virtual Event

    The Hudson River’s first lighthouse was built in 1826 at Stony Point. By the early 1900s, more than a dozen lights guided ships past the river’s islands and shallows. Seven of them still exist, including the Sleepy Hollow Lighthouse. Join author and photographer Kevin Woyce for a virtual tour of the Hudson River’s lighthouses, past …

    Free
  • Murder and Mayhem Walking Tour

    Sleepy Hollow Cemetery North Gate 540 North Broadway, Sleepy Hollow, NY, United States

    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
  • Home of the ‘Legend’

    Home of the ‘Legend’
    Sunnyside 3 W Sunnyside Lane, Irvington, NY, United States

    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
  • Octagon House Classic Tour

    Octagon House Classic Tour
    Armour-Stiner Octagon House 45 W Clinton Avenue, Irvington, NY, United States

    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
  • Philipsburg Manor Tours

    Philipsburg Manor Tours
    Philipsburg Manor 381 North Broadway, Sleepy Hollow, NY, United States

    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 farmers and twenty three enslaved individuals of African descent. Step into the gristmill and learn about the work of Caesar, the enslaved African miller. Tour …

    $12 – $17
  • Union Church Tours

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

    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 church. Henri Matisse’s last work, the Rose Window, and nine windows by Marc Chagall create a dramatic combination of light and color, art and spirituality. …

    $9
  • Octagon House Myths and Mysteries Tour

    Myths & Mysteries of The Octagon House
    Armour-Stiner Octagon House 45 W Clinton Avenue, Irvington, NY, United States

    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 Great Jack O’Lantern Blaze

    The Great Jack O’Lantern Blaze
    Van Cortlandt Manor 525 S Riverside Avenue, Croton-on-Hudson, NY, United States

    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
  • Irving’s Legend at Sunnyside

    Irving’s Legend at Sunnyside
    Sunnyside 3 W Sunnyside Lane, Irvington, NY, United States

    Irving’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 music and an appearance from the Headless Horseman himself make this a spooky spectacular experience for all ages! Advance reservations are required. No tickets will …

    $30 – $70
  • The Levin Brothers – Pete & Tony featuring Ali Ryerson

    Jazz Forum Club Performances
    Jazz Forum Club 1 Dixon Lane, Tarrytown, NY, United States

    As a French Horn major, Pete Levin earned a master’s degree from the Juilliard School. In the early ‘70s he switched to keyboards, becoming a synthesizer specialist in the New York City recording studio scene. Over the years, he has graced hundreds of jazz and pop recordings and performances by the likes of Miles Davis, …

    $25 – $30
  • The Legend – Cirque Theatre Performance

    The Legend Cirque
    East Parcel 60 Continental Street, Sleepy Hollow, NY, United States

    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
  • My Name is Not Mom: Meredith Masony, Tiffany Jenkins & Dena Blizzard

    Tarrytown Music Hall 13 Main Street, Tarrytown, NY, United States

    My Name is NOT Mom is a hilarious journey through motherhood with internet sensations Tiffany Jenkins, Meredith Masony and Dena Blizzard. After helping millions of fans get through the pandemic, this comic trio shares their take on mothering through the sleepless nights of the toddler years, middle school craziness and trying not to physically attack …

    $39 – $59
  • Sleepy Hollow Cemetery Lantern Tour

    Sleepy Hollow Cemetery Lantern Tour
    Sleepy Hollow Cemetery North Gate 540 North Broadway, Sleepy Hollow, NY, United States

    Soak 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 William Rockefeller, Andrew Carnegie, John Dustin Archbold and others resting in peace in the cemetery's north end. As this is only a one-hour tour, you’ll …

    $45
  • American Aristocrats Cemetery Tour

    American Aristocrats Cemetery Tour
    Sleepy Hollow Cemetery North Gate 540 North Broadway, Sleepy Hollow, NY, United States

    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 Levin Brothers – Pete & Tony featuring Ali Ryerson

    Jazz Forum Club Performances
    Jazz Forum Club 1 Dixon Lane, Tarrytown, NY, United States

    As a French Horn major, Pete Levin earned a master’s degree from the Juilliard School. In the early ‘70s he switched to keyboards, becoming a synthesizer specialist in the New York City recording studio scene. Over the years, he has graced hundreds of jazz and pop recordings and performances by the likes of Miles Davis, …

    $25 – $30

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.