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  • Sketching Light: Chagall’s Windows for Union Church

    Sketching Light: Chagall’s Windows for Union Church
    David Rockefeller Creative Arts Center 200 Lake Road, Tarrytown, NY, United States

    Sketching Light: Chagall’s Windows for Union Church provides a rare opportunity for visitors to explore the creative process of renowned artist Marc Chagall (1887-1985). In the 1960s, Chagall was commissioned by the Rockefeller family to create a large stained-glass window in memory of John D. Rockefeller, Jr., as well as eight smaller windows, for Union …

    Free
  • The Armour-Stiner Octagon House in Irvington is decorated with pumpkins for the fall season.

    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
  • Illuminated pumpkins at Great Jack O'Lantern Blaze in Croton-on-Hudson, New York

    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
  • Lyndhurst After Dark, a Halloween celebration, shows the mansion decorated in spooky fashion!

    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
  • An actor portrays Hulda of Bohemia during a performance of Hulda’s Night at Rockefeller State Park.

    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 tour pauses at the entrance to Archbold mausoleum.

    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
  • This is a black and white photo from the experimental play Peek-a-Boo (An Immersive Hudson Valley Haunt).

    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
  • A lantern tour in Sleepy Hollow Cemetery glides through a foggy night.

    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
  • This is a promotional montage for The Lone Bellow at Tarrytown Music Hall.

    The Lone Bellow – BY REQUEST ONLY Tour

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

    The Lone Bellow burst onto the scene with their self-titled debut in 2013. The Nashville-based trio (Zach Williams, Brian Elmquist, Kanene Pipkin) quickly became known for their transcendent harmonies, serious musicianship and raucous live performance — creating what NPR calls, 'earnest and magnetic folk-pop built to shake the rafters.' In 2015, the band released Then …

    $40 – $55
  • A view of the main entranct to Kykuit, the John D. Rockefeller mansion.

    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

  • Sketching Light: Chagall’s Windows for Union Church

    Sketching Light: Chagall’s Windows for Union Church
    David Rockefeller Creative Arts Center 200 Lake Road, Tarrytown, NY, United States

    Sketching Light: Chagall’s Windows for Union Church provides a rare opportunity for visitors to explore the creative process of renowned artist Marc Chagall (1887-1985). In the 1960s, Chagall was commissioned by the Rockefeller family to create a large stained-glass window in memory of John D. Rockefeller, Jr., as well as eight smaller windows, for Union …

    Free
  • The Armour-Stiner Octagon House in Irvington is decorated with pumpkins for the fall season.

    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

  • The Lady in White-An Immersive Octagon House Ghost Story

    The Lady in White-An Immersive Octagon House Ghost Story
    Armour-Stiner Octagon House 45 W Clinton Avenue, Irvington, NY, United States

    Her ship went down in flames, but the Lady in White returned to the Octagon House and still waits for her lover to find her there. In this immersive tour experience, a 1956 ghost story written by Carl Carmer, American author and longtime owner/resident of the Octagon House, unfolds while visitors explore the rooms of …

    $58

  • Tarrytown’s Trunk or Treat

    Tarrytown Recreation Center 238 West Main Street, Tarrytown, NY, United States

    For a little pre-Halloween fun, decorate your vehicle and give out candy to children of the community dressed in costumes! A best decorated car prize will be awarded. To participate, register. Your vehicle and supply your own candy to distribute. Children do not need to register in order to collect sugary treats. Just show up …

    Free
  • Illuminated pumpkins at Great Jack O'Lantern Blaze in Croton-on-Hudson, New York

    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
  • Lyndhurst After Dark, a Halloween celebration, shows the mansion decorated in spooky fashion!

    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
  • This is a promotional montage for Ossining’s Haunted Kill Trail of Terror and night market.

    Ossining’s Haunted Kill Trail of Terror

    Joseph G. Caputo Community Center 95 Broadway, Ossining, NY, United States

    Imagine strolling through the scenic Sing Sing Kill Greenway at dusk—peaceful, right? Wrong! Ossining’s “Haunted Kill” is here to ruin your sense of calm with 20 minutes of heart-pounding, scream-worthy thrills. As you wander through this rocky, shadow-filled path, historical ghost stories unfold before your eyes, brought to life by Westchester Collaborative Theater. But don’t …

    Free

  • 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
  • Headless Horseman poses next to statue of Rip van Winkle in Irvington, NY.

    Winkle vs. Horseman and Halloween Block Party

    110 Main Street 110 Main Street, Irvington, NY

    Halloween Block Party featuring Halloween crafts, games, a mirror maze, face painting, and shopping/activities for adults, including a beer garden hosted by Climbing Wolf! Also included are two 30-minute Rivertowns Playhouse performances of Rip Van Winkle and Legend of Sleepy Hollow. Costume contests happening throughout the night!. *Rain Date is Saturday, October 19, 2024 from 5:00-7:00pm.

    $15 – $25

  • Tarrytown Free Movie Night: The Nightmare Before Christmas

    Pierson Park 238 West Main Street, Tarrytown, NY, United States

    Following Tarrytown's Trunk or Treat, walk to Pierson Park for a free showing of Disney's The Nightmare Before Christmas! Popcorn available.

    Free
  • Twilight Village at Sleepy Hollow presents a Halloween market and cabinets of curiosities.

    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
  • An actor portrays Hulda of Bohemia during a performance of Hulda’s Night at Rockefeller State Park.

    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

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.