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

Irvington, NY

The Legend of Sleepy Hollow
Irvington Town Hall Theatre, 85 Main Street, Irvington, NY 10533

The stage performance that rocked sold-out shows last October is coming home to Sleepy Hollow. A headless ghost, an epic chase between rival suitors, and the hauntingly beautiful musical score will have you up out of your seat!

William Allen Jones’ THE LEGEND OF SLEEPY HOLLOW is a new musical based on the classic tale by Washington Irving. Don’t miss your chance to see this electrifying spin on the classic tale of Ichabod Crane and the Headless Horseman at the historic Irvington Town Hall Theatre–just a mile from the home of Washington Irving himself.

2019 dates: October 19, 20, 24, 25, 26, 2019.

Buy tickets: http://www.irvingtontheater.com/theatre or 914-591-6602

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. 2019 dates: April through November. Buy tickets online at www.sleepyhollowcemetery.org

In October, the cemetery hosts literary events featuring the work of Edgar Allan Poe and ghost stories by Washington Irving. For those over 21, there is Champagne Cocktails With the Dead, for children Spooky Stories!

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

Photo by Jennifer Mitchell

The Headless Horseman at Horseman’s Hollow. Photo by Jennifer Mitchell

Are 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 15 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 ($2/ticket surcharge for phone orders).

2019 dates: October 4-6; 11-13; 18-20; 25-27; 31; November 1-3.

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.

Admission for this 45-minute performance are by timed ticket only, which MUST be purchased in advance. Performances times vary by date. Buy tickets online at www.hudsonvalley.org or call 914-366-6900 ($2/ticket surcharge for phone orders). .

2019 dates: October 4-6; 11-14; 18-20; 25-27; 31; November 1-3.

Sleepy Hollow haunted hayrideHaunted 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.

2019 dates: October 25 and 26. Tickets go on sale late September.

Croton-on-Hudson, NY

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

The pumpkin Sea Serpent at The Great Jack O'Lantern Blaze. Photo by Tom Nycz

The pumpkin Sea Serpent at The Great Jack O’Lantern Blaze. Photo by Tom Nycz

The Hudson Valley’s biggest, most exciting, most electrifying Halloween event returns for an astounding 45 nights! See more than 10,000 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. Wander along our main street Pumpkin Promenade and stroll across the Pumpkin Zee Bridge. Gaze in wonder at swimming aquatic creatures and gasp at the sight of a giant Sea Serpent surfacing next to the Croton River. Get mesmerized by a color-changing star show in the plus-sized Pumpkin Planetarium. 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 ($2/ticket surcharge for phone orders).

2019 dates: Select Dates September – November 2019.

Tarrytown, NY

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

Lyndhurst_mansion_tarrytownThe Ghoul family has a bone to pick with you….that is, you’ve been formally invited to come and celebrate the spirit of the Halloween season with the Family in their House of Curiosities! They’re opening up their splendid and spooky castle home to those looking for a unique Halloween thrill this year. You’ll meet and interact with the ever peculiar Mr. and Mrs. of the Castle, see what Grandmama is cooking up, and find out what other zany family members have turned up at this festive time of year!

The 40-minute performances of Jay Ghoul’s House of Curiosities take place exclusively at night when the mansion comes alive through eerie lighting and Halloween decorations. While the evening experience will appeal to adults, teens, and school-aged children, this is not a Halloween haunted house – the scariest thing may just be the bad puns!

Buy tickets online at www.lyndhurst.org or call 914-631-4481 for information. All admissions are by timed ticket only, which MUST be purchased in advance.

2019 dates: October 17-20, 24-27, and on Halloween, October 31.

Sunnyside: Home of the ‘Legend’
Washington Irving’s Sunnyside, 89 West Sunnyside Lane, Tarrytown, NY.

Washington Irving's Sunnyside during Legend Behind the 'Legend.' Photo by Tom Nycz

Washington Irving’s Sunnyside during Legend Behind the ‘Legend.’ Photo by Tom Nycz

During October, Sunnyside celebrates its connection to Washington Irving’s classic tale, The Legend of Sleepy Hollow. This daytime event is the perfect prelude to an evening at Blaze, Horseman’s Hollow, or Irving’s “Legend.” As you tour both floors of Irving’s fascinating home, you will hear stories about what inspired Irving to write his most famous short story and see works of art inspired by The Legend of Sleepy Hollow. The tour also features a display of previously unseen objects from HHV’s collection—from special edition books to pop culture artifacts—related to the famous story. Historic games and Headless Horseman art activities are great for families. Concessions are also available for a picnic and a stroll through the Romantic landscape.

Tickets: $14; $12 for seniors; $10 for children 3-17. Free for Historic Hudson Valley members and children under 3. Buy tickets online at www.hudsonvalley.org or by phone at 914-366-6900 ($2/ticket surcharge for phone orders).

2019 dates: September 28-29; October 5-6; 12-14; 19-20; 26-27; November 2-3.

Tarrytown Music Hall Ghost Tours
Tarrytown Music Hall, 13 Main Street, Tarrytown, NY.

Unexplained happenings and paranormal activity have been experienced at our local 134-year-old historic theater—lights mysteriously turning back on after closing, the eerie sound of an unknown singer performing vocal scales in the wings after hours, high profile artists refusing to stay in one particular dressing room because they “sensed a presence.” Who or what could be the cause? Join this special “balcony to backstage” guided ghost tour to learn more about what’s been discovered about Tarrytown Music Hall, its intriguing history and the ghostly guests who still linger… if you dare!

The 45-minute tour kicks off in the lobby and includes climbing stairs and extended periods of standing. Please arrive 15 before scheduled tour time–no late entry will be permitted. Tickets $25.

2019 dates: October 15-16, 8 pm; October 18, 11 pm; October 22, 8 pm; October 26, 11 am, 12:30 pm, 2 pm, 3:30 pm, 5 pm; October 29, 8 pm.

Buy tickets: https://tickets.tarrytownmusichall.org or 877-840-0457

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!

2019 dates: to be announced.

Buy tickets online at www.thehistoricalsociety.net.