Irving’s Legend at Sleepy Hollow’s historic Old Dutch Church

Master storytellers offer dramatic performances of Washington Irving’s classic tale, featuring the Headless Horseman, Ichabod Crane, Brom Bones, and Katrina Van Tassel. Flavored with live spooky music, the spellbinding storytelling captivates all audiences. With Jonathan Kruk and Jim Keyes. Park at Philipsburg Manor and walk 1o minutes to Old Dutch Church. The show is 45 minutes long. October 4-6; 11-14; 18-20; 25-27; 31; November 1-3: 6:15, 7:30 & 8:45 pm on Fridays; 11:30am, 1:30, 3;30, 5, 6:30 & 8pm on Saturdays and Sundays.

More Halloween In Sleepy Hollow Country from Historic Hudson Valley

The Great Jack O’Lantern Blaze at Van Cortland Manor: The Great Jack O’Lantern Blaze is Historic Hudson Valley’s signature event and is a bucket list item for anyone in Westchester County. Whether your kids are young or in their teens, even if you have no kids at all – you have to check out  The Blaze at least once! More than 1,000 volunteers scoop, carve and light 7,000 pumpkins before they are hand-carved on site by a team of professional artists. Then they assemble them across the 18th century landscape of Van Cortland Manor in Croton-on-Hudson, creating a breathtaking display of illuminated jack o’lanterns.

There’s a 25-foot-tall jack o’lantern Statue of Liberty, a Pumpkin Carousel twirl, a Pumpkin Windmill whirl, and a Pumpkin Planetarium you can step inside that offers a star show. New this year is a Museum of Pumpkin Art, where classic paintings get the gourd treatment. See who let the (pumpkin) dogs out, listen for the Headless Horseman—and watch out for swooping jack o’lantern bats!

The jack o’lantern installation is enhanced by synchronized lighting and an original soundtrack. It is the highlight of all Halloween Events in Sleepy Hollow Country. BEWARE! This Event sells out!

The Blaze is open on select nights from September 20 to November 30:

Here’s the full schedule: September 20-22; 26-29; October 3-31; November 1-3; 8-10; 15-17; 22-23; 29-30 with timed entries from 7-9:30pm with timed entries every half-hour from 7-9:30pm.

Horseman’s Hollow at Philipsburg Manor

Another signature Sleepy Hollow Country event, from Historic Hudson Valley is Horseman’s Hollow. This premiere haunted event is our area’s top Boo-Fest for adults, teens and tweens and is also a threat to sell-out! At Horseman’s Hollow, you travel back in time to cursed Sleepy Hollow, an 18th-century village driven mad by the Headless Horseman! You will enter the foreboding gates and make your way through haunted landmarks like the cemetery, tavern, and Old Dutch Church. Be careful on your journey! The undead, the evil, and the insane rule this terrifying landscape. All paying homage to the Hessian who forever hunts his head. October 4-6; 11-13; 18-20; 25-27; 31; November 1- 3. Admission times: Every half-hour from 7-10pm

Selling Out Fast! The Sleepy Hollow Experience at Washington Irving’s Sunnyside 

After seven years of sold-out performances around the country, Brian Clowdus brings The Sleepy Hollow Experience to the home of the Legend.  In his production of Irving’s most famous ghost story, you will meet Ichabod Crane and Katrina Van Tassel. Along with a certain headless Hessian. Best of all Clowdus brings these characters home to the very place where the author imagined them. You will follow the characters from scene to scene with live music and a little bit of mayhem. And you will sip seasonal drinks and enjoy tasty treats at the Van Tassel’s harvest party. In a thrilling finale, see if you find out what really happens to Ichabod on the Sleepy Hollow Bridge. October 4-6, 10-13, 17-20, 24-27, 31; Nov 1-3 at 6:30 & 8:30pm.

The Unsilent Picture with Bill Irwin at Philipsburg Manor

Settle in to the Philipsburg Manor theater for this original short film based on Washington Irving’s ghostly tale “The Adventure of the Mysterious Picture.” Starring Tony Award-winner Bill Irwin and screened with live sound effects you have to see to believe, The Unsilent Picture explores what happens when a scientist’s convictions are put to the paranormal test. This Halloween cult picture bends reality in the true spirit of Sleepy Hollow. October 4-6; 11-14; 18-20; 25-27; 31; November 1- 3.  At 6, 7, 8, & 9pm Fridays through Sunday. Plus, 12:45, 2:45 & 4:45pm on Saturdays and Sundays.