Sleepy Hollow, New York
Best for: Iconic local traditions within driving distance of NYC
If you’re from New England, you’ve likely heard just how much Sleepy Hollow wakes up during the Halloween season. Just north of New York City along the Hudson, the village is forever tied to Washington Irving’s 1820 book The Legend of Sleepy Hollow, where the Headless Horseman sends Ichabod Crane, the main character, running for his life.
Stop by in October to walk the atmospheric grounds of Sleepy Hollow Cemetery by lantern light, visit the Old Dutch Church, see more of the iconic landmarks woven into Irving’s story, and catch the village’s famously robust Halloween programming. This year, the festivals and events are set to run through November 8, 2026. Of course, this includes the popular Great Jack O’Lantern Blaze, an evening where over 7,000 hand-carved, illuminated pumpkins line a half-mile riverside trail, complete with a pumpkin planetarium and a Headless Horseman display.
