Sponsored

  • 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
  • Victorian Tintype Portraits

    Victorian Tintype Portraits
    Lyndhurst 635 South Broadway, Tarrytown, NY, United States

    Back and expanded due to popular demand, this 2024 Halloween season is the chance to bring home a piece of photographic history. Victorian Photography Studio/Union Tintype and Hellcat Darkroom will be at Lyndhurst mansion ready to take your portrait using 19th-century photographic technology, resulting in a one-of-a-kind tintype portrait. Bring home a special memento of …

    $80 – $100
  • 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 (Sleepy Hollow)

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

    This two-hour tour will introduce you to the unique history of Sleepy Hollow and to some of the fascinating people who once lived in – or visited – our Village. The guides will lead you through our historic Hudson River village and regale you with tales about some of our local heroes and villains. Starting …

    $24.99
  • Witch’s Brew: Tea Blending Workshop With Belinda

    Sunnyside 3 W Sunnyside Lane, Irvington, NY, United States

    Delve into the mystical secrets of crafting delightful herbal infusions that tantalize the taste buds with with Belinda, our favorite doll at Washington Irving's Sunnyside, as your whimsical guide and Master Herbalist Karine Gordineer leading the way. CLASS LENGTH: 2 Hours AGE RECOMMENDATION: 14+ Participants will make three custom tea blends to take home in …

    $100
  • Gothic Harvest Market

    Gothic Market Weekend at Lyndhurst
    Lyndhurst 635 South Broadway, Tarrytown, NY, United States

    Explore the grounds of the historic Lyndhurst mansion and shop at the Gothic Harvest Market. Hudson Valley vendors will be selling an eclectic mix of spooky oddities, curated antiques, gothic jewelry, and witchy wares. You’ll have the opportunity to have a tarot reading and meet our resident roving vampire. Seasonal food offerings will also be …

    $25 – $35
  • 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
  • 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
  • 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
  • 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
  • Tarrytown Halloween Parade

    Patriots Park Patriots Park, Tarrytown, NY, United States

    Parking in the Villages of Tarrytown and Sleepy Hollow will be extremely limited on the night of the Halloween parade due to road closures. The Halloween Parade urges you to use Metro-North Railroad or Westchester County buses instead. The 22nd annual Village of Tarrytown Halloween Parade steps off at 5 pm from Patriot's Park. March south …

    Free
  • 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

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.