The best things to do in Sleepy Hollow this October

Hold on to your head!

After COVID-19 axed many Halloween celebrations in 2020, October festivities are back in historic Sleepy Hollow. And this year they’re not to be missed as the quaint Westchester County village — just 45 minutes from Manhattan — finally fetes the delayed bicentennial of the town’s namesake: Washington Irving’s short story “The Legend of Sleepy Hollow,” which was first published in 1820.

Irving would have related to the scheduling kerfuffle caused by COVID. After all, the Manhattan native was sent to the area to escape the city’s 1795 yellow fever epidemic at age 15, which is where he heard the old Dutch tales he later famously co-opted.

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

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

After Covid canned the Halloween fun last year, Sleepy Hallow is ready to celebrate.
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,” Mascia explained.

Those characters, inspired by locals, went on to become American archetypes.

“Brom Bones was the lovable bully,” said veteran storyteller Jonathan Kruk, who this year will bring “The Legend of Sleepy Hollow” to life outdoors at Sunnyside, Irving’s real-life home. “Ichabod Crane was the first nerd.”

When his iconic creepy tale was published in the expanded version of Irving’s collection of short stories and essays, “The Sketch Book of Geoffrey Crayon, Gent.,” it brought Irving fame and fortune after years of failure. He’d been unpopular as a local writer, especially after dubbing the local Dutch elite “Knickerbockers” — which conjured up images of old-fashioned knee-breeches at a time when slacks were the fad.

Dramatic performance of Washington Irving’s classic tale, "The Legend of Sleepy Hollow" will take place all month long.
A dramatic performance of Washington Irving’s classic tale “The Legend of Sleepy Hollow” will take place all month long.
courtesy Historic Hudson Valley.

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

Irving is also responsible for first calling New York City “Gotham,” the name of an English village where inhabitants feigned lunacy. That stuck too.

He even literally put Sleepy Hollow on the map: The village was officially North Tarrytown until 1996. Neighboring Irvington is named for the man himself. Walking tours of the village are available throughout October via the Historical Society, Inc. of Sleepy Hollow & Tarrytown. 

“Things are always pretty much about Irving around here,” said Mascia, who went to Sleepy Hollow High School. “Go Horsemen,” she cried, referring to the school’s football team, whose gruesome mascot is a headless horseman. “I think Irving would have been a great person to chitchat with. He was very tongue in cheek; he didn’t take everything too seriously.”

Here’s how to get in on all the October fun — even if you’re not up on your Irving.

The entire village is getting in on the Halloween fun.
The entire village is getting in on the Halloween fun.
Margaret Fox Photography

‘Bicentennial Blues’ evening talks at Sleepy Hollow Cemetery

This year, the village is dubbing their main attraction “Bicentennial Blues” because COVID robbed revelers of celebrating the 200th birthday of “The Legend of Sleepy Hollow”.

To make up for it, a speaker will impersonate the dryly humorous Irving and reminisce about his “fabulous adventures and amazing career” with talks among the tombstones in the village cemetery throughout the month.

Oct. 1, 2, 8, 9, 29 and 30 from 7:30–9 p.m. $40 per person. Sleepy Hollow Cemetery, 540 N. Broadway; 914-631-0081, SleepyHollowCemetery.org/Special-Events/

Tour the Old Dutch Church and cemetery

Cemetery tours are available both day and night.
Cemetery tours are available both day and night.
James Logan

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

Stroll through for free in the daytime, or take a guided tour on weekends. For full spooky effect, try a nighttime lantern tour — kids under 10 are not permitted — which are operated daily through October and Saturdays and Sundays through November. These fill up quickly, so book in advance.

Daily through October and Saturdays and Sundays through November. $15 per person. Old Dutch Church, 430 N. Broadway; 914-631-4497, SleepyHollowCemetery.org

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

Sleepy Hollow Haunted Hayride and Block Party

Jump aboard a hay wagon and travel down Albany Post Road past the Old Dutch Church — the exact route Ichabod Crane took as he was pursued by the Headless Horseman.

Once the wagon glides into the dark of the woods, anything could happen…

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

Wagon rides are available Oct. 22 and 23, and there’s a block party on Beekman Avenue both of those nights featuring live music, entertainment, family activities and vendors.

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

Make sure to book early because this one’s popular.

Oct. 22 and 23 5-11 p.m. $40 per person. Sleepy Hollow Village Hall/Firehouse, 28 Beekman Ave.; SleepyHollowNY.gov

Step inside Washington Irving’s home, Sunnyside

This year, for the first time, veteran storyteller Jonathan Kruk will bring “The Legend of Sleepy Hollow” to life outdoors at Sunnyside.
Veteran storyteller Jonathan Kruk is bringing Irving’s story to life at Sunnyside.
Margaret Fox Photography

Head on, ahem, past the statue of the Headless Horseman — a definite selfie magnet — and join a tour, led by a costumed interpreter, of Irving’s home, Sunnyside.

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

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

“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, Tim Burton’s included. It’s authentic.”

Fridays, Saturdays and Sundays Oct. 1-31, 6:30, 8 and 9:30 p.m. $10 for adults and $8 for seniors and children. 3 W. Sunnyside Lane, Irvington; HudsonValley.org

Great Jack O’Lantern Blaze at Van Cortlandt Manor

If you’re willing to branch out from Sleepy Hollow, Van Cortlandt Manor in nearby Croton-on-Hudson is hosting the monumental Great Jack O’Lantern Blaze.

Set in an 18th-century landscape, the installation features more than 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 created from glowing pumpkins, and there’s even an immersive river display.

Select nights from Sept. 17 to Nov. 21. $48 for adults and $40 for children. Van Cortlandt Manor, 525 S. Riverside, Croton-on-Hudson; HudsonValley.org/Events/Blaze

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