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  • 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 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 at the Music …

    $25
  • 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 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 at the Music …

    $25
  • 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, …

    $20
  • 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

    Bigger, Brighter, and More Spectacular Than Ever Before! 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. Complete …

    $24 – $50
  • Sleepy Hollow Cemetery Lantern Tour

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

    Step back in time and explore the cemetery by kerosene lantern light! This two-hour evening tour gives you a great overview of why Sleepy Hollow Cemetery is so famous. You’ll visit titans of industry like Andrew Carnegie and William Rockefeller, meet Washington Irving whose famous short story gave our village its very name, see the …

    $50
  • Spooky Board Games

    Spooky Board Games
    New Kawaii 1 Bridge Street, Suite 105, Irvington, NY, United States

    Game Night at New Kawaii Join us on Wednesdays at 7PM for Game Night for Grown Ups and Young Adults (teens are welcome!) All October: Dare to Roll! The midweek gets menacing! Wednesdays in October are dedicated to horror gaming — every week, a new way to test your courage and roll through the fright. …

    $5
  • The Wailers 2025 Natural Mystic 30th Anniversary Tour

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

    The Wailers are a rare breed of musicians who have earned their place in the annals of music history. Their culture-defining music, embodying the spirit of the 70s reggae movement, has left an indelible mark on the industry. Experience the magic of their timeless classics and incredible cuts from Bob Marley’s vast repertoire in a …

    $44 – $64
  • 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 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 at the Music …

    $25
  • 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, …

    $20
  • 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

    Bigger, Brighter, and More Spectacular Than Ever Before! 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. Complete …

    $24 – $50
  • Murder and Mayhem Walking Tour

    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 of Sleepy Hollow Cemetery 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 …

    $60
  • Sleepy Hollow Cemetery Lantern Tour

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

    Step back in time and explore the cemetery by kerosene lantern light! This two-hour evening tour gives you a great overview of why Sleepy Hollow Cemetery is so famous. You’ll visit titans of industry like Andrew Carnegie and William Rockefeller, meet Washington Irving whose famous short story gave our village its very name, see the …

    $50
  • ShadowDark with a Dark(er) Twist

    ShadowDark with a Dark(er) Twist
    New Kawaii 1 Bridge Street, Suite 105, Irvington, NY, United States

    Looking for Players - no long-term commitment! Join DM Kevin for ShadowDark on Thursdays at 7 PM This October, the dice hold dark secrets… Join us for a run of horror one-shots across Shadowdark universe. Monsters, mysteries, and mayhem await — and every session is a different fright-filled adventure. No experience necessary. Characters can be …

    $10
  • Witch, Please!

    Irvington Theater Performances
    Irvington Theater 85 Main Street, Irvington, NY, United States

    Run amok at this Halloween Drag Spectacular at The Irvington Theater on October 9th. Featuring local and national drag performers as your favorite Halloween icons, an appearance by 'The Sanderson Sisters', and meet & greet with Shannon Carlin, Author of “Witches Run Amok”  Disney’s Official Oral History of the film Hocus Pocus + local vendors, …

    $33.85 – $71.21
  • Sierra Hull & John Craigie – Northeast Autumn 2025

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

    Sierra Hull is a six-time IBMA Mandolin Player of the Year, two-time Grammy nominee, and one of the most dynamic voices in bluegrass and Americana. Her latest album, A Tip Toe High Wire, marks a bold new chapter - her first independent release, showcasing her songwriting and instrumental prowess. With guest appearances by Béla Fleck, …

    $45.50 – $65.50
  • 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 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 at the Music …

    $25
  • The Headless Horseman Files

    The Headless Horseman Files
    Philipsburg Manor 381 North Broadway, Sleepy Hollow, NY, United States

    Immerse yourself in this Sleepy Hollow whodunit and decide for yourself what really happened to Ichabod Crane. Follow your guide on a mysterious 45-minute walk through the historic grounds of Sleepy Hollow’s Philipsburg Manor, where you’ll step into a chilling, live-action 18th-century whodunit. Along the way, encounter suspicious townsfolk like fiery Hans Van Ripper, charming …

    $25 – $30
  • 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, …

    $20
  • An Audience with Poe

    An Audience with Poe
    Historic Hudson Valley 639 Bedford Road, Tarrytown, United States

    Sip, savor, and shiver with Poe’s darkest tales brought to life through storytelling, cocktails, and confections. This fall, professional storytellers bring to life the “powerful graphic effect” that Washington Irving once praised in Edgar Allan Poe’s writing, with haunting renditions of The Raven, The Tell-Tale Heart, The Black Cat, and The Masque of the Red …

    $60
  • 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

    Bigger, Brighter, and More Spectacular Than Ever Before! 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. Complete …

    $24 – $50
  • Spirits of Sleepy Hollow Country

    Spirits of Sleepy Hollow Country
    Philipsburg Manor 381 North Broadway, Sleepy Hollow, NY, United States

    A Night of Legendary Magic Featuring Mark Clearview & Nick Wallace Join master illusionists as they journey into the realm of the unknown at this spooky supernatural spectacle. Their tricks and conjurings will leave you spellbound as they communicate with the spirits of Sleepy Hollow Country, like Hulda of Bohemia, British spy Major John Andre, …

    $65
  • Sleepy Hollow Rock & Roll House of Horrors

    Sleepy Hollow Rock & Roll House of Horrors
    Holy Cross Parish Hall 116 Beekman Avenue, Sleepy Hollow, NY, United States

    Descend in to the basement of an abandoned church rectory and witness new scares with new twists!!! Be careful what you wish for…Enter if you dare! Get your tickets now. 2025 Dates: weekends 10/4 through 11/1. Times vary by date, consult organizer's website for exact times of entry.

    $30 – $35
  • An Evening with Edgar Allan Poe

    An Evening with Edgar Allan Poe
    Sleepy Hollow Cemetery North Gate 540 North Broadway, Sleepy Hollow, NY, United States

    The famous author, who lived his last few years in a cottage 20 miles from Sleepy Hollow Cemetery, rises from the dead for an evening of mystery and macabre. Poe, portrayed by Sleepy Hollow's master storyteller David Neilsen, will read favorites from his own stories and poems. This event always draws a crowd – purchase tickets in …

    $45
  • Twilight Village at Sleepy Hollow

    Twilight Village at Sleepy Hollow
    Philipsburg Manor 381 North Broadway, Sleepy Hollow, NY, United States

    Where the Legend Lives After Dark! As evening settles over Philipsburg Manor, channel the spirit of Irving’s famously creepy tale at this immersive outdoor experience with live storytellers, fire performers, and eerie encounters around every corner. Mingle with Legend icons Ichabod Crane and Katrina Van Tassel, wander through a pop-up market with curious goods, oddities, and …

    $25 – $30
  • Sherlock Holmes and the Legend of Sleepy Hollow

    Sherlock Holmes and the Legend of Sleepy Hollow
    Makers Central 84 Central Avenue, Tarrytown, NY, United States

    In this spine-tingling and laugh-filled theatrical thrill ride, Sherlock Holmes and Dr. John Watson leave the foggy streets of London behind for the eerie woods of Sleepy Hollow! A rash of bizarre crimes—and rumors of the Headless Horseman’s ghostly return—have the local villagers terrified. But as Holmes digs deeper, even he begins to question what’s …

    $50

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.