Sleepy Hollow sits on the east bank of the Hudson River, just north of Tarrytown and close enough to New York City for an easy day trip. Its name is doing a lot of work: Washington Irving set The Legend of Sleepy Hollow in this low valley of old Dutch farms, churchyards, and wooded roads.
The village is not just a Halloween stage set. The Old Dutch Church and the adjacent cemetery are real 17th-century survivals, and the headstones and maples still give the place its best atmosphere. A few minutes away, Philipsburg Manor tells a harder Hudson Valley story of Dutch trade, milling, and enslaved labour.
North and east of the village, the Rockefeller presence is everywhere: Kykuit, the hilltop family estate, the stained glass at Union Church, Stone Barns, and the carriage roads of Rockefeller State Park Preserve. Come in October if you want the full Headless Horseman circus, but the quieter seasons are better if you want to see the place itself.