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  • TarryHollow: Sleepy Hollow, Irving and the Old Dutch Church

    418 North Broadway 418 North Broadway, Sleepy Hollow, United States

    Embark on a captivating journey through the rich history of Sleepy Hollow, where the echoes of colonial America come to life. Join our local historical society for a 90-minute immersive walking tour, starting with the tale of the first Dutch settlers who lived on Philipsburg Manor, one of the largest colonial estates in the Hudson …

    $25
  • Classic Daytime Cemetery Tour

    Classic Daytime Cemetery Tour
    Sleepy Hollow Cemetery South Gate 430 North Broadway, Sleepy Hollow, NY, United States

    Soak up the beauty of this 176-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 way "to have a colloquy among the tombs" as Washington Irving, famous author of "The Legend of Sleepy Hollow", did himself back in 1849. You'll …

    $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
  • Eric D’Alessandro

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

    Eric D’Alessandro, a charismatic New Yorker with an unfiltered sense of humor, a camera, and a knack for storytelling, has etched his name into the hearts of comedy lovers across the nation. His unique comedic style, infused with his Italian-American heritage, spins raw, relatable narratives that resonate with the everyday American. From his early beginnings …

    $45 – $65
  • Hulda’s Night at Rockefeller State Park Preserve

    Hulda’s Night at Rockefeller State Park Preserve
    Park Manager Residence 25 Sleepy Hollow Road, Sleepy Hollow, NY, United States

    Hulda's Night at Rockefeller State Park Preserve is like nothing else you've ever experienced. Step back in time on this very special night in the woods of the real Sleepy Hollow! You walk through the gathering gloom, your path lit only by lanterns. The dark woods surround you as the chill night air settles in. Your …

    $68
  • 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
  • Lyndhurst After Dark!

    Lyndhurst After Dark!
    Lyndhurst 635 South Broadway, Tarrytown, NY, United States

    Lyndhurst After Dark offers an exquisite Halloween experience, blending gothic charm with subtle spookiness. You've experienced the splendor of the Lyndhurst Mansion during the day, but have you seen it draped in candlelight? This Halloween Season, experience the history of the Mansion and explore Victorian lore in the glow of an October evening: Lyndhurst After …

    $20 – $40
  • 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
  • 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
  • The Legend of Sleepy Hollow at Old Dutch Church

    The Legend of Sleepy Hollow at Old Dutch Church
    Old Dutch Church 430 North Broadway, Sleepy Hollow, NY, United States

    Don’t miss your chance to experience "The Legend of Sleepy Hollow" in the heart of Sleepy Hollow! On October 11, 12, 18, 19, 25, and 26 at 7 p.m., the historic Old Dutch Church becomes the perfect stage for Washington Irving’s haunting tale. With glowing lanterns and spellbinding performances, you'll encounter iconic characters like Ichabod …

    $40
  • 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
  • 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
  • Hulda’s Night at Rockefeller State Park Preserve

    Hulda’s Night at Rockefeller State Park Preserve
    Park Manager Residence 25 Sleepy Hollow Road, Sleepy Hollow, NY, United States

    Hulda's Night at Rockefeller State Park Preserve is like nothing else you've ever experienced. Step back in time on this very special night in the woods of the real Sleepy Hollow! You walk through the gathering gloom, your path lit only by lanterns. The dark woods surround you as the chill night air settles in. Your …

    $68
  • Sleepy Hollow Haunted Hayride

    Sleepy Hollow Haunted Hayride
    Sleepy Hollow Village Hall 28 Beekman Avenue, Sleepy Hollow, NY, United States

    Climb aboard Sleepy Hollow’s annual Haunted Hayride and hold on to your head! All seems well when you board your hay wagon in the brightly lit streets of downtown Sleepy Hollow. Rumbling off into the dark you realize too late you are heading down the Albany Post Road past the Old Dutch Church, following exactly Ichabod Crane’s flight from …

  • Peek-a-Boo (An Immersive Hudson Valley Haunt)

    Peek-a-Boo (An Immersive Hudson Valley Haunt)
    Bethany Arts Community 40 Somerstown Road, Ossining, NY, United States

    After a sold-out run in 2024, River’s Edge Theatre Company is bringing its provocative immersive show Peek-a-Boo back to Bethany Arts Community this October. Inspired by hidden histories of the Hudson Valley, this one-of-a-kind theatrical experience is brimming with intimate encounters, voyeuristic thrills, and deeply human performances. Written by Meghan Covington (Artistic Director of River’s …

    $30 – $35
  • Comedy with Seth Herzog & Alex Moffat

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

    Join Irvington Theater for an all-star night of smart, high-energy comedy featuring two of New York's most hilarious and dynamic performers: Seth Herzog ("30 Rock," "Broad City,") and Alex Moffat (“SNL”). Seth Herzog is known for his sharp wit and wild storytelling. He produces one of NYC's longest-running, monthly comedy shows, "Sweet," and is a …

    $33
  • Eric D’Alessandro

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

    Eric D’Alessandro, a charismatic New Yorker with an unfiltered sense of humor, a camera, and a knack for storytelling, has etched his name into the hearts of comedy lovers across the nation. His unique comedic style, infused with his Italian-American heritage, spins raw, relatable narratives that resonate with the everyday American. From his early beginnings …

    $45 – $65
  • 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
  • Irvington Farmers Market

    Irvington Farmers Market
    Main Street School 101 Main Street, Irvington, NY, United States

    Enjoy 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 local produce, seafood and meats, cheese, pickles, prepared foods and baked goods. The Irvington Farmers Market is just a short distance from Washington Irving’s home …

    Free
  • Classic Daytime Cemetery Tour

    Classic Daytime Cemetery Tour
    Sleepy Hollow Cemetery South Gate 430 North Broadway, Sleepy Hollow, NY, United States

    Soak up the beauty of this 176-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 way "to have a colloquy among the tombs" as Washington Irving, famous author of "The Legend of Sleepy Hollow", did himself back in 1849. You'll …

    $30
  • Warner Library Fall Book Sale

    Warner Library Book Sale
    Warner Library 121 North Broadway, Tarrytown, NY, United States

    Visit the Warner Library on Saturday, October 18, and Sunday, October 19, from 10 am to 5 pm for the Friends of the Warner Library Book Sale. The Friends will be selling gently used paperback and hardcover books, CDs, and DVDs. The proceeds from the book sale support children’s, young adult, and adult programs at …

    Free

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.