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Called North Tarrytown until 1996 when its residents voted to change its name, the village of Sleepy Hollow lies on the east bank of the Hudson, where the river widens to form the Tappan Zee. Although it’s actually not the setting for Washington Irving’s short story “The Legend of Sleepy Hollow,” (a distinction which belongs to neighboring Tarrytown) the village has bragging rights that go beyond its connection to American folklore.
Hardly a sleepy little town, Sleepy Hollow has charm galore. Locals and visitors flock to the trendy shops and restaurants that line Beekman Avenue, the village’s main street. With its proximity to the Hudson River as well as hills, valleys, lakes and forests, the town lures outdoor enthusiasts for myriad recreational activities, including hiking, boating, skiing, rock climbing and white-water rafting. Take a picnic basket to Kingsland Point Park off Palmer Avenue, where lighthouse aficionados enjoy tours of the furnished 1883 lighthouse on some Sundays for a small fee; phone (914) 366-5109 for schedule.
Attend open-mike night or a reading by a well-known author at the Hudson Valley Writers’ Center, 300 Riverside Dr., in the restored 1912 Philipse Manor railroad station. The center presents poetry performances, workshops and literary events throughout the year at its headquarters and at various local venues; phone (914) 332-5953 for information.
The village celebrates its namesake tale with several annual events. In late October, the headless horseman pays a visit to Philipsburg Manor along with thousands of other guests for Horseman’s Hollow. Creep around the grounds lit by bonfires and lanterns and expect to bump into witches, ghosts and other ghoulish beings.
What better place to go for a haunted hay ride than Sleepy Hollow? Crowds gather at Sleepy Hollow Village Hall, 28 Beekman Ave., on select weekends in October for a thrilling experience that combines tales of Ichabod Crane with Hudson River Valley history.

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