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  • 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 Original Knickerbocker Tour

    The Original Knickerbocker Tour
    Sleepy Hollow Cemetery South Gate 430 North Broadway, Sleepy Hollow, NY, United States

    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
  • Ghost Tours of Tarrytown Music Hall

    Ghost Tours of Tarrytown Music Hall
    Tarrytown Music Hall 13 Main Street, Tarrytown, NY, United States

    Join this guided tour created by Master Storyteller Jonathan Kruk, and discover the historic lore and spirits that linger here at The Tarrytown Music Hall. The Tarrytown Music Hall was built in 1885 during the Millionaire’s Colony Era when mansions dotted the Hudson Valley landscape and families such as the Rockefellers, Goulds and Vanderbilts gathered …

    $31
  • Ghost Tours of Tarrytown Music Hall

    Ghost Tours of Tarrytown Music Hall
    Tarrytown Music Hall 13 Main Street, Tarrytown, NY, United States

    Join this guided tour created by Master Storyteller Jonathan Kruk, and discover the historic lore and spirits that linger here at The Tarrytown Music Hall. The Tarrytown Music Hall was built in 1885 during the Millionaire’s Colony Era when mansions dotted the Hudson Valley landscape and families such as the Rockefellers, Goulds and Vanderbilts gathered …

    $31
  • 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
  • Dracula and the Theater of Doom

    Dracula and the Theater of Doom
    Tarrytown Music Hall 13 Main Street, Tarrytown, NY, United States

    Dracula, the King of the Vampires, is loose in the Tarrytown Music Hall this Halloween! This new breathtaking thrill ride, written and directed by Sleepy Hollow’s own Peter Royston, keeps the audience on its feet as they move with the characters from eerie space to space through the historic Tarrytown Music Hall! Join the audience …

    $31
  • 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
  • Randy Brecker Quintet featuring Ada Rovatti

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

    Jazz 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 albums by a wide range of artists from James Taylor, Bruce Springsteen and Parliament/Funkadelic to Frank Sinatra, Steely Dan, Jaco Pastorius and Frank Zappa. Saxophonist …

    $30 – $35
  • 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
  • Murder Mystery!

    Murder Mystery!
    Sleepy Hollow Cemetery North Gate 540 North Broadway, Sleepy Hollow, NY, United States

    Somebody's dead at Sleepy Hollow Cemetery (actually, a lot of people are dead--it is a cemetery) and it's up to YOU to bring the killer to justice! Everyone who attends is a suspect--even you! All attendees will receive a unique identity ahead of time (in case anyone wants to wear a costume) complete with secrets …

    $55
  • 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 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
  • The Jayhawks

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

    The Jayhawks kick off the October lineup at Tarrytown Music Hall. The Jayhawks and their rootsy sound were definitely swimming against the tide when they emerged from a crowded Minnesota music scene in 1985. Over the course of almost 4 decades, 11 albums, countless memorable live shows and enough personal drama to fill a couple …

    $38 – $68
  • Dracula and the Theater of Doom

    Dracula and the Theater of Doom
    Tarrytown Music Hall 13 Main Street, Tarrytown, NY, United States

    Dracula, the King of the Vampires, is loose in the Tarrytown Music Hall this Halloween! This new breathtaking thrill ride, written and directed by Sleepy Hollow’s own Peter Royston, keeps the audience on its feet as they move with the characters from eerie space to space through the historic Tarrytown Music Hall! Join the audience …

    $31
  • 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
  • Randy Brecker Quintet featuring Ada Rovatti

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

    Jazz 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 albums by a wide range of artists from James Taylor, Bruce Springsteen and Parliament/Funkadelic to Frank Sinatra, Steely Dan, Jaco Pastorius and Frank Zappa. Saxophonist …

    $30 – $35
  • 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
  • Randy Brecker Quintet featuring Ada Rovatti

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

    Jazz 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 albums by a wide range of artists from James Taylor, Bruce Springsteen and Parliament/Funkadelic to Frank Sinatra, Steely Dan, Jaco Pastorius and Frank Zappa. Saxophonist …

    $30 – $35
  • TaSH Farmers Market

    Tarrytown and Sleepy Hollow Farmers Market
    Patriots Park Patriots Park, Tarrytown, NY, United States

    Fresh Hudson Valley produce, meat, bread, honey, specialty foods, cut flowers, dairy products, beer and wine. There is live music and sometimes demonstrations of traditional crafts. Route 9 (Broadway) next to the Warner Library. Free parking across the street at John Paulding School. Saturdays, 8:30 am to 1:30 pm rain or shine. Well behaved dogs …

    Free
  • History of Rockwood Hall

    History of Rockwood Hall
    Rockwood Hall Phelps Way, Pleasantville, NY, United States

    Join Rockwood docent David Teich on an adventure into the past as he explores Rockwood Hall and its rich history through stories of the land and the people who called it home. Former estate of William Rockefeller, this site boasts scenic views overlooking the Hudson, lush forests, and remnants of 19th century luxuries. Leashed dogs …

    $3
  • Sleepy Hollow Street Fair

    Beekman Avenue, Sleepy Hollow Beekman Avenue, Sleepy Hollow, NY, United States

    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 time to visit Sleepy Hollow. The weeks leading up to Halloween have something for everyone: haunted hayrides, Gothic mansions, blazing pumpkins, farmers markets, live music, 5K …

    Free
  • 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
  • Kykuit Tours

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

    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
  • 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

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.