One of the most exciting, charming and highly anticipated fall traditions in the Hudson Valley is The Great Jack O’Lantern Blaze.
If you have never heard of it or had the chance to visit this unique legendary experience in the historic Van Cortlandt Manor, make it a plan to do so this autumn.
It is presented by the Historic Hudson Valley, Westchester County’s largest cultural organization that educates and entertains visitors through school programs, tours of four National Historic Landmarks, and a wide variety of legendary experiences.
Even though our children are grown now and have moved away, several friends of ours plan an evening to meet up, see the displays and grab a bite to eat, all at the same location. Now we have shared this fun event with our grandchildren that live out of state. When they come to visit us they know I always have something unique planned for them, especially when we visit the many wonderful activities planned by the Historic Hudson Valley. Perfect for adults, families with children and friends looking for something different to do one evening, this is a walk along a long trail of illuminated pumpkin displays in event history.
Across Sleepy Hollow Country, a full slate of immersive events celebrates the season and the enduring legacy of Washington Irving’s classic ghost story, “The Legend of Sleepy Hollow.”
At The Great Jack O’Lantern Blaze, running for 44 nights in Croton-on-Hudson from Sept. 18 to Nov. 8, the expanded path features exciting new attractions. The Creature Feature Forest pays tribute to Van Cortlandt Manor's history as home to a drive-in movie theater in the mid-20th-century, inviting visitors to meet a cast of classic movie monsters carved entirely from pumpkins.
Nearby, Literary Lane reimagines familiar fables, giving classic children’s tales a whole new glow. On the lawn of the site’s regal manor house, visitors are invited to an interactive dance party. As part of its 2026 expansion, the event is more accessible than ever, with expanded value pricing of just $24 on select evenings. Trailside, the VIP hospitality experiences The Gourd & Goblet Tavern and Headless Horseman's Hideaway return with all-new menus. This year, the Monster's Mug pops up along the path, serving quick drinks for visitors.
The Great Jack O’Lantern Blaze is presented by Con Edison. Contributing Sponsors include JPMorgan Chase and Northwell Phelps Hospital. Hospitality Partners are Windrose on Hudson and Tarrytown House Estate. Beverage Sponsors include Captain Lawrence and Hudson North Cider Co. Media Sponsors are WHUD and The Peak.
The Hudson Valley is a breathtaking location year-round, but I think the fall season is the most beautiful.
During October the colors are vibrant, the air is crisp and there are exciting activities that enable visitors to be able to experience the magic of the season with a lineup of unforgettable events and tours taking place throughout the month. They are all easy to combine with a visit to The Great Jack O’Lantern Blaze.
At Washington Irving’s Sunnyside, daytime Legendary Tours offer family fun, including a shadow puppet film and a Legend-themed exhibit. By night, master storyteller Jonathan Kruk and musician Jim Keyes team up for the outdoor performances of Irving’s ‘Legend,’ a dramatic retelling of Irving’s classic tale. At Philipsburg Manor, professional illusionists conjure the supernatural during The Spirits of Sleepy Hollow Country: A Night of Legendary Magic, with all-new magic and special effects. By popular demand, The Headless Horseman Files: A Sleepy Hollow Whodunit expands its run this year and adds new morning offerings, giving even more visitors the chance to gather clues and uncover what really happened to Ichabod Crane.
Twilight Village at Sleepy Hollow returns to Philipsburg Manor with more vendors and more activities than ever, alongside its signature fire performers, storytellers, and a dramatic sound-and-light show recreating the Horseman's midnight ride.
And at the Historic Hudson Valley Library, An Audience with Poe returns for an evening of storytelling and cocktails inspired by Edgar Allan Poe, pairing haunting renditions of “The Raven,” “The Tell-Tale Heart,” “The Black Cat,” and “The Masque of the Red Death” with complimentary themed drinks and treats.
All events have limited capacity and regularly sell out; advance ticket purchase is required. Tickets are now on sale at hudsonvalley.org.
The Great Jack O' Lantern Blaze: Hudson Valley features illuminated, individually hand-carved jack o’ lanterns in elaborate, professionally lit displays throughout the historic landscape of Van Cortlandt Manor.
The Gourd & Goblet Tavern is a sit-down VIP hospitality experience set in an 18th-century inn nestled along the pumpkin trail. It includes table service with delicious snacks, cocktails and mocktails. The Tavern experience is recommended for ages 18 and older.
The Headless Horseman’s Hideaway is a spirited stop on the pumpkin trail that includes festive snacks plus cocktails or mocktails. Photo-ops with the Headless Horseman are included in this VIP experience, which is recommended for all ages. Details: The Spirits of Sleepy Hollow Country: A Night of Legendary Magic Featuring nationally renowned illusionists Mark Clearview and Nick Wallace, this magic show features all-new tales and plenty of audience interactions. Snacks and drinks including alcoholic beverages are available to purchase. Premium tickets include a complimentary snack and beverage as well as cabaret style seating.
Details: Twilight Village at Sleepy Hollow — At Philipsburg Manor in the heart of Sleepy Hollow, Twilight Village features traveling musicians and performers, a robust market with food, drink, and souvenirs, and plenty of photo-ops, including with the Headless Horseman.
The Headless Horseman Files: A Sleepy Hollow Whodunit — on this 45-minute walk through the historic grounds of Sleepy Hollow’s Philipsburg Manor, visitors encounter suspicious townsfolk—each with their own tale and motive for causing the demise of Ichabod Crane. Visitors work together to mine the clues and decide who they think the Headless Horseman really is. Details: Irving’s ‘Legend’ - Performing amid the lush landscape of Washington Irving’s estate, master storyteller Jonathan Kruk, accompanied by professional musician Jim Keyes, brings to life the story of The Legend of Sleepy Hollow in this outdoor, evening event, a perennial favorite. Snacks and drinks including alcoholic beverages will be available to purchase.
Details: Legendary Tours of Washington Irving’s Sunnyside - Sunnyside celebrates its connection to Washington Irving’s classic tale, “The Legend of Sleepy Hollow,” at this family-friendly daytime event. Visitors can tour the cottage, see an original short shadow puppet film, and enjoy a Legend-themed exhibit. You must be 21 years old to purchase alcohol at their sites and events. Proof of ID is required.
About Historic Hudson Valley: Historic Hudson Valley, Westchester County’s largest cultural organization, educates and entertains visitors through school programs, tours of four National Historic Landmarks, and a wide variety of legendary experiences.
Van Cortlandt Manor is at 525 South Riverside Ave., just off Route 9 in Croton-on-Hudson. Philipsburg Manor is at 381 North Broadway in Sleepy Hollow. Washington Irving’s Sunnyside is on West Sunnyside Lane, off Route 9 in Irvington.
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