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The village of Sleepy Hollow did not exist when Washington Irving wrote “The Legend of Sleepy Hollow,” but many of the locations in the gruesome tale sit within its current borders. Your first stop on a Headless Horseman tour should be the Old Dutch Reformed Church, a 17th-century stone chapel that’s listed on the National Register of Historic Places. It’s usually open during the month leading up to Halloween, but infrequently the rest of the year. The adjacent churchyard is where the Headless Horseman was supposedly laid to rest, galloping through the countryside to return there every night before dawn.
Nearby Sleepy Hollow Cemetery is where Washington Irving himself is buried, surrounded by a wrought-iron fence inscribed with his family’s name. Because various Gilded Age families spent weekends in the country in and around Sleepy Hollow, Irving is surrounded by various Carnegies, Chryslers, and Rockefellers.
Speaking of Rockefellers, Sleepy Hollow is the gateway to the Rockefeller State Park Preserve, which includes a 45-mile-long network of carriage roads donated by the Rockefeller family. Rockwood Hall, the massive mansion that belonged to William Avery Rockefeller, Jr., was torn down in 1941, but you can still gaze down on the Hudson River and Palisades from where it stood. We recommend a not-too-taxing stroll along 13 Bridges Loop Trail, a 2-mile hike past bridges crossing the Gory Stream.
Also making an appearance in “The Legend of Sleepy Hollow” is Philipsburg Manor. At this 19th-century grist mill, a stone’s throw from Old Dutch Reformed Church, Ichabod Crane tries to impress some local ladies with his intellect. Today, it’s an open-air museum that tells the story of the region’s once-thriving mill trade.
