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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
  • 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
  • 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
  • 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
  • Octagon House Tour with Reading of ‘The Raven’

    ‘Tis the Wind and Nothing More
    Armour-Stiner Octagon House 45 W Clinton Avenue, Irvington, NY, United States

    "Tis the Wind and Nothing More" Anything can happen if you let the madness take over. This Halloween weekend, step back in time and tour The Armour-Stiner Octagon House with one of its most mysterious residents as your guide. In this immersive tour experience, the enigmatic (and possibly insane) Jessie Clarke revisits her final home, …

    $58
  • 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
  • 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
  • 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 Dark! …

    $20 – $40
  • 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
  • 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
  • The Legend of Sleepy Hollow – a Radio Play

    The Legend of Sleepy Hollow – a Radio Play
    The Chapel at Scarborough Presbyterian Church 671 Scarborough Road, Briarcliff Manor, United States

    The Legend of Sleepy Hollow - a Radio Play is an adaptation of Washington's Irving classic work. Eight actors perform almost every word of the original short story, and also work as foley (sound effects) artists. Live music performed by Blake Rowe helps to set the scene. The "live studio audience" will be transported back …

    $20
  • 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
  • The Robert Cray Band – Groovin’ for 50 Years!

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

    Blues icon. Soul man. Rock and roller. Robert Cray is all these things – and more. The Georgia- born, Washington-raised musician first picked up a guitar after seeing The Beatles on TV then, having witnessed Jimi Hendrix perform in Seattle, determined that his destiny would also follow a similar path. And so he has: across …

    $51 – $141
  • 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
  • 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
  • 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
  • Scarecrow’s Ball

    The Good Witch Coffee Bar 134 Southside Avenue, Hastings-On-Hudson, NY, United States

    The Good Witch Coffee Bar's Scarecrow’s Ball is an all-day, Oz-themed Halloween extravaganza with a dash of magic and a sprinkle of mischief. It’s got everything from “witchy” brews to a costume contest, perfect for those who think their scarecrow outfit is next-level fabulous. The day kicks off with a Drag Queen Story Hour (because …

    Free
  • Sleepy Hollow Halloween 10K & Kids Fun Run

    Morse School 30 Pocantico Street, Sleepy Hollow, NY, United States

    Enjoy a remarkable course that takes you through Historic Sleepy Hollow’s treasured sights including a stretch along the Hudson River with views of the Headless Horseman Bridge, Sleepy Hollow Cemetery and the Old Dutch Church. You never know what might be lurking on the course in Sleepy Hollow… Registration is limited to the first 2000. …

    $40 – $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.