Halloween in Sleepy Hollow

There’s something for everyone during Sleepy Holloween: haunted hayrides, Gothic mansions, blazing pumpkins, farmers markets, live music, street fairs, parades, and of course, the Headless Horseman. Read on for some of our favorite October treats in Sleepy Hollow Country. See our big calendar of events for even more things to see and do.


Featured Sleepy Hollow Halloween Events

Sleepy Hollow, NY

Sleepy Hollow Cemetery Tours
Tours offered April through November.

Sleepy Hollow Cemetery lantern tour

Sleepy Hollow Cemetery lantern tour

Take an evening lantern tour of the final resting place of author Washington Irving in the famous Sleepy Hollow Cemetery. Creep though the winding roads and soaring monuments that peek through the shadows of the night. For those of us who remember the Gothic soap opera Dark Shadows, here is your chance to enter the crypt of vampire Barnabas Collins. You may also visit a Revolutionary War militia captain, a notorious counterfeiter, a noted spiritualist, industrialists Andrew Carnegie and William Rockefeller, and others. 2016 dates: April through November. Buy tickets online at www.sleepyhollowcemetery.org

Horseman’s Hollow
Philipsburg Manor, 381 North Broadway (Route 9), Sleepy Hollow, NY

dsc_0536Are you ready to be scared out of your mind?

Taking the tale of the Legend of Sleepy Hollow to its darkest extremes, Horseman’s Hollow returns for 14 terrifying evenings! For the month of October, the 300-year-old Philipsburg Manor transforms into a fearsome landscape ruled by vampires, witches, undead soldiers, ghouls, and ghosts, all serving the Headless Horseman himself!

Visitors begin walking a haunted trail, stumbling upon scary scenes of a town driven mad by the Headless Horseman. The Hollow’s unfortunate inhabitants are all too ready to keep visitors from ever leaving.

Creatures, some human and some not, lurk in the shadows, ready to terrify the unsuspecting, while incredible special effects disorient and unsettle. Heads will roll…maybe even your own!

This event is NOT suitable for small children or for the faint of heart, but it is Sleepy Hollow’s premiere haunted attraction, right in the heart of the village. Stocked with professional actors and state-of-the-art special effects, Horseman’s Hollow has a very high fear factor. You have been warned!

All admissions are by timed ticket only, which MUST be purchased in advance. Buy tickets online at www.hudsonvalley.org or call 914-366-6900. 2016 dates: Oct. 7-9, 14-16, 21-23, 27-31.

Irving’s ‘Legend’
Old Dutch Church, Sleepy Hollow, NY. Park at Philipsburg Manor lot.

Master storyteller Jonathan Kruk offers a dramatic performance of Washington Irving’s classic tale, “The Legend of Sleepy Hollow,” featuring the Headless Horseman, Ichabod Crane, Brom Bones, and Katrina Van Tassel. Flavored with live spooky organ music by Jim Keyes, Kruk’s storytelling captivates all audiences. Admissions for this 45-minute performance are by timed ticket only, which MUST be purchased in advance. Performances times vary each evening. Buy tickets online at www.hudsonvalley.org or call 914-366-6900. Advance purchase is essential. 2016 dates: Oct. 7-9, 14-16, 21-23, 28-31.

Haunted HayrideSleepy Hollow haunted hayride
Sleepy Hollow Village Hall, 28 Beekman Avenue, Sleepy Hollow, NY 10591, 914-366-5100.

Climb aboard Sleepy Hollow’s annual Haunted Hayride and watch out for the Headless Horseman! Join the block party on Beekman Avenue before or after your hair-raising ride through the real Sleepy Hollow. Contact Village of Sleepy Hollow recreation department for tickets and information, www.sleepyhollowny.gov, 914-366-5109. 2016 dates: to be announced.


Croton-on-Hudson, NY

The Great Jack O’ Lantern Blaze
Van Cortlandt Manor, 525 South Riverside Avenue, Croton-on-Hudson, NY.

The Skeleton Emergence Photo © Bryan Haeffele

The Skeleton Emergence
Photo © Bryan Haeffele

The Hudson Valley’s biggest, most exciting, most electrifying Halloween event returns for a whopping 30 nights! See more than 7,000 individually hand-carved, illuminated jack o’ lanterns in an elaborate walk-through experience. Meander through an 18th-century riverside landscape and discover a breathtaking display. Stroll through the Tunnel O’ Pumpkin Love and witness the incredible sight of gourd-filled Jack-in-the-Boxes springing up and bouncing around. See slithering ground snakes, a giant spider web, and go gaga over a collection of shrunken Little Monsters. Gaze in amazement at a towering pumpkin bonfire and a working doomsday grandfather clock. All made of jack o’ lanterns! Tens of thousands of visitors came to last year’s sold-out Blaze. Complete with original, atmospheric music, sound effects, and professional lighting, this is the tri-state area’s largest and most innovative Halloween happening. All admissions are by timed ticket only, which MUST be purchased in advance. Buy tickets online at www.hudsonvalley.org or call 914-366-6900.

2016 dates: Sept. 30, Oct. 1-2, 7-10, 13-16, 19-31, Nov. 3-6, 10-13.

Tarrytown, NY

Jay Ghoul’s House of Curiosities
Lyndhurst, 635 South Broadway, Tarrytown, NY.

Lyndhurst_mansion_tarrytownCome visit the Disenchanted Castle with all new decorations and theme this year! If you’ve always dreamed of living in a castle, you better think twice! Castle dwellers including Maleficent, Dracula, Henry VII, those Hogwarts Wizards and the Wicked Witch will let you in on the real secrets of being a haunted ghoul. Experience the only indoor Halloween venue in Westchester. Meet the cast of characters as they lead you on a half-hour spooky performance through the first floor and basement of Lyndhurst mansion. Guest will be able to experience the spectacular gothic castle at night with eerie lighting and fabulous seasonal decorations in a way rarely seen.

Buy tickets online at www.lyndhurst.org or call 914-631-4481 for information. 2016 dates: to be announced.

The Legend Behind the “Legend”
Washington Irving’s Sunnyside, 89 West Sunnyside Lane, Tarrytown, NY. For GPS: 3 West Sunnyside Lane, Irvington, NY 10533.

Washington Irving's Sunnyside

Washington Irving’s Sunnyside

A daytime visit here is the perfect prelude to an evening at The Great Jack O’Lantern Blaze, Horseman’s Hollow, or Irving’s ‘Legend.’ Irving’s fascinating home—a colorful blend of architectural styles—will showcase numerous objects related to Irving’s famous story and other tales. Visitors on Saturday and Sunday can enjoy a shadow puppet performance of The Legend of Sleepy Hollow and experience one of Irving’s spooky tales on a walk through the woods. Tickets: $12; $10 for seniors; $6 for children 3-17. Free for Historic Hudson Valley members and children under 3. 2016 dates: to be announced.

TarryHollow: Walking Through Time
Historical Society, 1 Grove Street, Tarrytown, NY 10591, 914-631-8374.

Truth is stranger than fiction as you walk through the villages of Tarrytown and Sleepy Hollow–and that says a lot for a place with a reputation for headless horsemen! Hear tales both spectral and earthly of the mystical and unexplained incidents of the area’s eerie and legendary past. Past residents have left ghostly marks on the community, and a few of them may still linger nearby!

Two-hour walking tours cover parts of downtown Tarrytown and Sleepy Hollow. Wear comfortable shoes and be prepared for a brisk walk!

2016 dates: to be announced.

Buy tickets online at www.thehistoricalsociety.net.