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  • 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
  • Marty Stuart and His Fabulous Superlatives w/ special guest Richard Shindell

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

    Marty Stuart is an American country and bluegrass music singer, songwriter, and musician. Active since 1968, Stuart initially toured with Lester Flatt, and then in Johnny Cash's road band before beginning work as a solo artist in the early 1980s. His greatest commercial success came in the first half of the 1990s on MCA Records …

    $52 – $72
  • 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
  • TaSH Farmers Market

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

    Stop by TaSH, Tarrytown’s and Sleepy Hollow’s weekly farmers market, for fresh Hudson Valley produce, meat, bread, cut flowers, dairy products, preserves, wine, and beer. There are weekly live music performances, children’s events as well as ongoing educational activities and programs. Don’t miss the weekly free samplings! Well behaved dogs are welcome, provided your pooch is …

    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
  • Christ Church/San Marcos 186th Annual Fall Fair

    Christ Church San Marcos 43 South Broadway, Tarrytown, NY, United States

    Christ Episcopal Church in Tarrytown, where Washington Irving once worshipped, is thrilled to bring back its Fall Fair in 2025! From 10 am to 4 pm, visitors can shop for books, browse the White Elephant section for bargains, go thrifting for vintage fashion, jewelry, toys, and more. Don’t forget to stop by the International Café …

    Free
  • 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
  • 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
  • Christ Church Tour

    Christ Church Tour
    Christ Church San Marcos 43 South Broadway, Tarrytown, NY, United States

    Tour the historic church where Washington Irving was a vestryman, warden, Sunday School teacher, and regular parishioner until his death in 1859. The ivy on the church walls is from cuttings taken at Irving’s home, Sunnyside, and his pew is still marked in the front of the sanctuary. An estimated 5,000 descended on this small …

    Free
  • 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
  • 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
  • Spooky (but not too) Scary Stories

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

    What makes kids Happy for Halloween? SPOOKY (But not too) SCARY STORIES! Told by Legendary Storyteller, Jonathan Kruk at the Tarrytown Music Hall. Frightful fun with tales of the The Witch’s Surprise, Rolly-Head, the Haunted Hand, with live eerie music, and Jumpstarts! Jonathan Kruk is renowned for telling tales of the headless horseman and finger …

    $29
  • Indie RPG One-Shot: Never Going Home

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

    Characters will be provided for this one-shot. Limited seats - early registration is highly recommended. Adults and teens 16+ Join New Kawaii for the next entry in our monthly Indie RPG series - a perfect for the month of October, it's a horror RPG! Never Going Home is a party-focused role-playing game set in horror-haunted …

    $10
  • 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

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.