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  • Spirits of Sleepy Hollow Country

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

    Join us at Philipsburg Manor, nestled in the heart of Sleepy Hollow Country, for an extraordinary evening of mystery and illusion. Experience the magic of The Spirits of Sleepy Hollow Country as acclaimed illusionists Mark Clearview and Nick Wallace weave a spellbinding tapestry of intrigue and wonder, inspired by the legends and lore of Sleepy …

    $60
  • 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 – $55
  • 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

    A Night of Folklore, Fortune, and Festivities! Looking for the true heart of Sleepy Hollow? You’ll find it at Twilight Village at Sleepy Hollow. Discover delightful and mysterious creatures who will tell your fortune, croon creepy tunes, and tell tall-ish tales of legends and lore. Shop for super Sleepy Hollow swag at the Halloween night …

    $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 19-20 and 26-27 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 by Kerin McCue and Jeremy Goldsmith, you'll encounter iconic characters …

    $40
  • An Evening with Amanda Palmer

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

    Amanda Palmer is a singer, songwriter, playwright, pianist, author, director, and blogger who simultaneously embraces and explodes traditional frameworks of music, theatre, and art. She first came to prominence as part of the punk cabaret duo The Dresden Dolls, earning global applause for their inventive songcraft and wide-ranging theatricality. Her solo career has proven equally …

    $44 – $64
  • 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 …

    $62
  • 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
  • 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

    River’s Edge Theatre Company and Bethany Arts Community are teaming up yet again to bring a spooky, immersive theatre production to Westchester this fall. Peek-a-Boo, written by Meghan Covington (Artistic Director of River’s Edge Theatre Company) and directed by Jessica Irons (Artistic Director of Theater O) is an experimental new play inspired by the real …

    $30 – $35
  • The Man Behind the Legend

    The Man Behind the Legend
    Sleepy Hollow Cemetery North Gate 540 North Broadway, Sleepy Hollow, NY, United States

    Meet the man behind the Legend! In his most famous short story Washington Irving says of Sleepy Hollow Country, "If ever I should wish for a retreat whither I might steal from the world and its distractions, and dream quietly away the remnant of a troubled life, I know of none more promising than this …

    $45
  • 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
  • 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 breathtaking horror comedy, now in its THIRD SHOCKING YEAR at the Music Hall, keeps the audience on their feet as they move with the characters from eerie space to space! Join the audience as it follows Dracula, Van Helsing, and …

    $36
  • 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 …

    $24.99
  • Tarryhollow: Walking Through Time (Tarrytown)

    Historical Society Walking Tours
    Patriots Park Patriots Park, Tarrytown, NY, United States

    This two-hour tour will introduce you to the unique history of Tarrytown and Sleepy Hollow and to some of the most intriguing people who have ever lived here. The guides will lead you through the many sections of historic Tarrytown and regale you with enticing tales of local lore. Starting from Patriots Park, you will …

    $24.99
  • Kykuit Tours

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

    A majestic paradise with sweeping river views. See the Hudson Valley’s top cultural attraction! Built between 1906 and 1913, Kykuit was home to four generations of the Rockefeller family, beginning with the philanthropist John D. Rockefeller, founder of Standard Oil. His business acumen made him, in his day, the richest man in America. Now a …

    $25 – $75
  • 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 19, and Sunday, October 20, 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 will support children’s, young adult, and adult programs …

    Free
  • Legend of Sleepy Hollow Family Storytelling Event

    Legend of Sleepy Hollow Family Storytelling Event
    Hudson Valley Writers Center 300 Riverside Drive, Sleepy Hollow, NY, United States

    Storyteller David Neilsen will perform a 25-minute retelling of Washington Irving’s "The Legend of Sleepy Hollow". In costume, Neilsen uses Irving’s original language to set the scene and take the audience on a ride along with Ichabod Crane on that fateful night. This will be a fun, family event, featuring additional Halloween treats and activities …

    $20
  • Myths & Mysteries of The Octagon House

    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 celebrates the Halloween season …

    $29
  • Tarryhollow: Walking Through Time (Tarrytown)

    Historical Society Walking Tours
    Patriots Park Patriots Park, Tarrytown, NY, United States

    This two-hour tour will introduce you to the unique history of Tarrytown and Sleepy Hollow and to some of the most intriguing people who have ever lived here. The guides will lead you through the many sections of historic Tarrytown and regale you with enticing tales of local lore. Starting from Patriots Park, you will …

    $24.99
  • Haunted Objects Live!

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

    Chilling, True Tales from the Newkirk Museum of the Paranormal! Are you ready to uncover the chilling true stories behind the world’s most haunted objects? Join Greg and Dana Newkirk (Travel Channel’s Kindred Spirits, Amazon Prime’s Hellier) at Tarrytown Music Hall for an interactive presentation that will leave you on the edge of your seat. …

    $45 – $55
  • 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 …

    $24.99
  • Spirits of Sleepy Hollow Country

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

    Join us at Philipsburg Manor, nestled in the heart of Sleepy Hollow Country, for an extraordinary evening of mystery and illusion. Experience the magic of The Spirits of Sleepy Hollow Country as acclaimed illusionists Mark Clearview and Nick Wallace weave a spellbinding tapestry of intrigue and wonder, inspired by the legends and lore of Sleepy …

    $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

    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 with synchronized lighting and an original soundtrack, don't …

    $20 – $57
  • Rock N Roll House of Horrors

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

    Are you brave enough for the six terrifying rooms at Rock N Roll House of Horrors in Sleepy Hollow? Tickets are selling fast, so grab yours and face the fear—if you dare!   (Please note - the stage is set with animatronics and props. There is no live band playing.)

    $25 – $45

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.