Historic Hudson Valley brings legends to life this fall

Channel the spirit of Irving's creepy tale at Twilight Village, an immersive outdoor experience with live storytellers, fire performers and eerie encounters around the Headless Horseman. (Courtesy Historic Hudson Valley )

By LAURA SCHILLER 

Storytellers are part of the evening marketplace at Twilight Village. 

You know fall has arrived when pumpkin spice fills the grocery aisles, porches sprout hay bales and Van Cortlandt Manor glows with the light of more than 7,000 hand-carved jack-o’-lanterns. 

Now in its 21st year, the Historic Hudson Valley ”Great Jack O’Lantern Blaze” attracts around 125,000 visitors on 52 nights between Sept. 12 and Nov. 16, all eager to marvel at its spectacular displays of glowing gourds.

Upon entering the 18th-century landscape in Croton-on-Hudson, guests wander at their own pace along an illuminated trail, encountering creations like a life-sized T. rex, a 24-foot spider web, a planetarium, a spinning carousel and Ferris wheel and an astonishing menagerie of dragons, owls, elephants, witches and glowing undersea creatures, all meticulously carved and lit from within.

For 2025, Blaze introduces a massive emerald-hued “Wizard of Oz” dreamscape plus a circus big-top, retro video games and iconic New York landmarks including the Statue of Liberty and Empire State Building. 

A new hospitality offering also makes its trailside debut: the Headless Horseman’s Hideaway, serving spooky sips and snacks alongside an encounter with Sleepy Hollow’s most infamous rider, who doesn’t mind selfies. And at the Gourd & Goblet Tavern, an 18th-century inn, guests who choose the VIP experience can enjoy a cocktail or bite while soaking in the atmosphere.

“Blaze has been running since 2005, and it’s grown enormously,” said Rob Schweitzer, Historic Hudson Valley’s director of communications & commerce. “But the heart of it remains the same — walking through an extraordinary historic landscape at night, seeing what our team of only 10 artisans can do with thousands of pumpkins. This year’s new displays are going to surprise even our returning visitors.”

The Great Jack O’Lantern Blaze is located at 525 South Riverside Ave., Croton-on-Hudson. For tickets and more information, visit hudsonvalley.org.

While the Great Jack O’Lantern Blaze remains the crown jewel of Historic Hudson Valley’s fall calendar, the nonprofit is rolling out even more seasonal offerings across its sites this year, including several new immersive theatrical events. 

“We’re always inspired by Washington Irving’s works, and we’re constantly asking ourselves how we can create events that feel fresh and unique,” said Schweitzer. “We try to move away from the typical haunted house model and instead offer something more imaginative and truer to Irving’s legacy.”

At Philipsburg Manor in Sleepy Hollow, for example, daytime visitors can experience the Headless Horseman Files, a 45-minute interactive mystery walk that invites guests to investigate what really happened to the main character, Ichabod Crane, in Irving’s “The Legend of Sleepy Hollow.” Along the way, townsfolk played by live actors drop cryptic clues, whispers circulate through the crowd and ultimately the Horseman himself looms large.

“This experience is part walking tour, part theater and part whodunit,” said Schweitzer. “The original story leaves Ichabod’s fate a mystery, and we’re inviting guests to explore that in a playful way.”

Philipsburg Manor is located at 381 North Broadway, Sleepy Hollow. For tickets and more information, visit hudsonvalley.org.

Philipsburg also hosts Twilight Village, where fire jugglers, storytellers and musicians transform the property into a festive evening marketplace. Visitors can browse vendors selling oddities and crafts, sample comfort food and mocktails or seek insight from a tarot reader, all just in time for the Headless Horseman to make his dramatic entrance.

Back by popular demand, illusionists Mark Clearview and Nick Wallace return to Philipsburg Manor with ”Spirits of Sleepy Hollow Country: A Night of Legendary Magic.” This supernatural stage show conjures eerie encounters with legendary figures like Hulda the Witch, Major André and the Headless Horseman, blending sleight of hand, storytelling and spine-tingling surprises. 

In Irving’s Legend — which takes place at Washington Irving’s Sunnyside — audiences can experience master storyteller Jonathan Kruk’s enchanting outdoor retelling of “The Legend of Sleepy Hollow,” complete with live music and shadowy supporting characters. 

“Every fall, people want to come here and live inside the world Washington Irving created,” said Schweitzer. “We’re proud that people come from all 50 states to experience these events, where everyone can find something magical — whether it’s wandering among glowing pumpkins, hearing Irving’s words under the stars or solving a mystery with the Headless Horseman lurking nearby.”

Washington Irving’s Sunnyside is located at 3 West Sunnyside Lane, Irvington.  For tickets and more information, visit hudsonvalley.org.

Though some events are best suited for ages 8 or 10 and up, all programming is created with families in mind. Tickets for many of these events are sold only in advance and sell fast, so be sure to plan.