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  • 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
  • Eric Walton: Mentalist & Magician

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

    Eric Walton — hailed by the New York Times as an “erudite magician and rabble rouser” — brings his world class mentalism to Irvington Theater. An award-winning and critically-acclaimed entertainer, Walton has performed his singular brand of mentalism, mystifying feats of mind-reading, and magic for audiences of all kinds. "A masterclass in card magic and …

    $33
  • 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 …

    $65
  • 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
  • The Good, the Bad and the Unusual-Cemetery Tour

    The Good, the Bad and the Unusual-Cemetery Tour
    Sleepy Hollow Cemetery North Gate 540 North Broadway, Sleepy Hollow, NY, United States

    Join Sara Mascia and Tara Van Tassell from our local historical society as they dish about several intriguing locals as well as some of Sleepy Hollow Cemetery's world-famous inhabitants. You can guess who will be good, bad, or unusual! Among the many locals are poet and eccentric Minna Irving, chocolatier William Wallace, and popular neighbor …

    $45
  • The Machine Performs Pink Floyd: 50 Years of Wish You Were Here

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

    The Machine has forged a 30+ year reputation of extending the musical legacy of Pink Floyd. The New York-based quartet performs a diverse mix of The Floyd's extensive 16-album repertoire, complete with faithful renditions of popular hits as well as obscure gems. With stellar musicianship and passionate delivery, The Machine explores collective improvisation rivaling that of …

    $42 – $58
  • 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
  • Walk for Wishes: A Sleepy Hollow Family Fun Fall Festival

    Kingsland Point Park 299 Palmer Avenue, Sleepy Hollow, NY, United States

    Walk for Wishes: A Sleepy Hollow Family Fun Fall Festival returns on October 5, 2025, from 9am-2pm at Kingsland Point Park, bringing a heartwarming, Halloween-themed celebration for all ages to the scenic Hudson River waterfront. Join Make-A-Wish Hudson Valley for this family-friendly fundraiser that brings together wish families, volunteers, sponsors, and the community to raise …

  • 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
  • Paint a Headless Horseman Pumpkin with Heather Gleason

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

    Join Halloween artist Heather Gleason as she teaches you the step-by-step process of painting your own pumpkin-shaped Headless Horseman! Each participant will receive a 11 x 10" wood pumpkin, brushes and acrylic paints to create their very own artwork. NO EXPERIENCE NECESSARY. Have fun painting while supporting the historic Sleepy Hollow Cemetery and its residents. …

    $80
  • 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
  • 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
  • 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
  • Deconstructing Dark Side of the Moon

    The Ark at the Shames JCC 371 South Broadway, Tarrytown, NY, United States

    In this multimedia lecture, musicologist Scott Freiman will deconstruct this groundbreaking album on its 50th anniversary. Scott will take you on a track-by-track journey through Pink Floyd’s masterpiece that pushed the boundaries of rock music, incorporating elements of jazz, classical, and experimental music. You’ll learn about the inspiration for and evolution of the songs that …

    $25 – $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 …

    $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
  • 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
  • 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
  • Bored Teachers: The Struggle Is Real! Comedy Tour

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

    Bored Teachers are BACK with all new material on their “The Struggle is Real!” Comedy Tour. For years, Bored Teachers Studios has brought a sense of humor to teachers around the world to ease their daily struggle in the classroom. They’ve amassed over a billion views on their viral videos on social media, over 10 …

    $54.50 – $71.50
  • Pacifica Quartet with Sharon Isbin, guitar

    Friends Of Music Concerts
    Kusel Auditorium at Sleepy Hollow High School 210 North Broadway, Sleepy Hollow, NY, United States

    With a career spanning three decades, the multiple Grammy Award-winning Pacifica Quartet has achieved international recognition as one of the finest chamber ensembles performing today. The quartet is known for its virtuosity, exuberant performance style, and often-daring repertory choices. Having served as quartet-in-residence at Indiana University’s Jacobs School of Music for over a decade, the …

    $40

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.