The Best Things to Do in Sleepy Hollow in October

Hold your head!

After COVID-19 halted many Halloween celebrations in 2020, the October festivities are back in historic Sleepy Hollow. And this year, don’t miss them, as the quaint village of Westchester County—just 45 minutes from Manhattan—finally celebrates the postponed bicentennial of the city’s namesake: Washington Irving’s short story “The Legend of Sleepy Hollow,” which was first published in 1820.

Irving is said to have had to deal with the planning squabble caused by COVID. After all, the Manhattan native was sent to the area to escape the yellow fever epidemic of 1795 at age 15, where he learned the old Dutch tales he later famously co-opted.

“Irving was an impressionable teenager,” said Sara Mascia, executive director of the… Historical Society, Inc. from Sleepy Hollow & Tarrytown, who organized the ill-fated bicentennial ceremonies. “He really connected with the people here and heard the stories they would tell.”

In 2020, Sleepy Hollow was set to host several events, including a literary conference, to honor the man who introduced Ichabod Crane and the gory Headless Horseman to the masses, who now draw thousands of tourists to “Horror Hollow.”

After COVID canned the Halloween fun last year, Sleepy Hallow is ready to celebrate.
Margaret Fox Photography

“He fought in the War of 1812, and in 1814 he was stationed on Staten Island, where he met a soldier named Ichabod Crane, and he created the character,” explains Mascia.

Those characters, inspired by the locals, became American archetypes.

“Brom Bones was the sweet bully,” said veteran storyteller Jonathan Kruk, who will be bringing this year “The Legend of Sleepy Hollowto the great outdoors in Sunnyside, Irving’s real home. “Ichabod Crane was the first nerd.”

When his iconic scary story was published in the expanded version of Irving’s collection of short stories and essays, “Geoffrey Crayon’s sketchbook, Ghent.,” it brought Irving fame and fortune after years of failure. He hadn’t been popular as a local writer, especially after calling the local Dutch elite ‘Knickerbockers’, evoking images of old-fashioned knee-breeches at a time when trousers were all the rage.

A dramatic performance of Washington Irving’s classic tale, “The Legend of Sleepy Hollow” takes place throughout the month.
courtesy of Historic Hudson Valley.

“Some people didn’t like being called that, but it stuck. Look at the New York Knicks,” Mascia said.

Irving is also responsible for New York City being first referred to as “Gotham,” the name of an English village where the inhabitants pretended to be mad. That also stuck.

He even literally put Sleepy Hollow on the map: the village was officially North Tarrytown until 1996. Neighboring Irvington is named after the man himself. Village walking tours are available throughout October through the Historical Society, Inc. from Sleepy Hollow & Tarrytown.

“It’s always kind of about Irving here,” said Mascia, who attended Sleepy Hollow High School. “Go Riders,” she shouted, referring to the school’s soccer team, whose gruesome mascot is a headless rider. “I think Irving would have been a great person to chat with. He was very tongue-in-cheek; he didn’t take everything too seriously.”

Here’s how to join in on all the October fun — even when you’re not on your Irving.

The whole village joins in the Halloween fun.
The whole village joins in the Halloween fun.
Margaret Fox Photography

‘Bicentennial Blues’ Evening Readings at Sleepy Hollow Cemetery

This year, the village is calling their main attraction “Bicentennial Blues” because COVID has deprived revelers from celebrating the 200th anniversary of “The Legend of Sleepy Hollow”.

To make up for it, a speaker will impersonate the dry-humorous Irving and reminisce about his “fantastic adventures and great career” with readings between the headstones in the village cemetery throughout the month.

1, 2, 8, 9, 29 and 30 October from 19:30 – 21:00 $40 per person. Sleepy Hollow Cemetery, 540 N Broadway; 914-631-0081,

Visit the Old Dutch church and cemetery

Cemetery tours are available both during the day and at night.
Cemetery tours are available both during the day and at night.
James Logan

A tour of the Old Dutch Church, founded in 1685, and the adjacent Sleepy Hollow Cemetery, which contains Irving’s grave, is a must.

Walk through for free during the day, or take a guided tour at the weekend. For completely spooky effect, try a nighttime lantern tour — children under 10 are not allowed — which run daily through October and Saturdays and Sundays through November. These fill up quickly, so book in advance.

Daily until October and Saturday and Sunday until November. $15 per person. Old Dutch Church, 430 N. Broadway; 914-631-4497,

Tours include a visit to Irving's grave.
Tours include a visit to Irving’s grave.
James Logan

Sleepy Hollow Haunted Hayride and Block Party

Hop aboard a harvestman and drive along Albany Post Road past the Old Dutch Church – the exact route Ichabod Crane took when he was chased by the Headless Horseman.

Once the car slides into the dark of the forest, anything can happen…

Take a selfie with the Headless Horseman.
Take a selfie with the Headless Horseman.
James Logan

wagon rides are available October 22 and 23, and there will be a block party on Beekman Avenue both nights with live music, entertainment, family activities, and vendors.

The Sleepy Hollow hayride is one of the most popular events in the area.
The Sleepy Hollow hayride is one of the most popular events in the area.
Margaret Fox Photography

Make sure to book early as it is popular.

October 22 & 23 5pm-11pm $40 per person. Sleepy Hollow Village Hall/Fire Station, 28 Beekman Ave.;

Step Inside Washington Irving’s House, Sunnyside

This year, for the first time, veteran storyteller Jonathan Kruk will
Veteran storyteller Jonathan Kruk brings Irving’s story to life in Sunnyside.
Margaret Fox Photography

Continue, ahem, past the statue of the Headless Horseman—an obvious selfie magnet—and take a guided tour, led by a costumed interpreter, of Irving’s home, Sunnyside.

Irving bought his idyllic home in 1835. It preserves the man’s genius presence, especially in his office and library, where he wrote his later works, including his extensive biography of President George Washington.

This year, veteran storyteller Jonathan Kruk will bring “The Legend of Sleepy Hollow” to life outdoors in Sunnyside for the first time.

“I tell the story, but I don’t read it,” said Kruk. “I add drama and use quotes from Irving. It’s more true to the story than the movies, including Tim Burton. It’s authentic.”

Friday, Saturday and Sunday October 1-31, 6:30 PM, 8 AM and 9:30 PM $10 for adults and $8 for seniors and children. 3 W. Sunnyside Lane, Irvington;

Awesome Jack O’Lantern Blaze at Van Cortlandt Manor

If you’re willing to head out of Sleepy Hollow, Van Cortlandt Manor in nearby Croton-on-Hudson hosts the landmark Great Jack O’Lantern Blaze.

Set in an 18th-century landscape, the installation features over 7,000 illuminated, hand-carved jack o’ lanterns, synchronized lighting and an original soundtrack.

For the first time this year, the event will feature a New York City skyline made of glowing pumpkins, and there’s even an immersive river display.

Select nights from September 17 to November 21. $48 for adults and $40 for children. from Cortlent Manor, 525 S. Riverside, Croton on Hudson;


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