In October, visitors flock to this Hudson River-facing village for gorgeous foliage, Halloween events, and to celebrate Washington Irving’s famous literary work, “The Legend of Sleepy Hollow.” The village is just as enjoyable the rest of the year — with fewer crowds — for its water views, casual eateries, and history in spades, from famed cemeteries to the county’s most impressive historic home.
10 a.m. Grab a quick bite at Los Andes Bakery (180 Valley St). The Chilean shop — look for a sign reading simply “Valley Bakery” — serves traditional pastries like flaky empanadas and sweet alfajores, buttery cookies held together by a layer of dulce de leche.
10:30 a.m. Pick up a free map at the south gate or office to help you navigate the 90 arboreal acres of Sleepy Hollow Cemetery (540 N Broadway). Among the tombstones and stone angels, you’ll find grand mausoleums belonging to titans of industry and the monied elite, including Walter Chrysler, William Avery Rockefeller, and Harry and Leona Helmsley. Also buried here: Elizabeth Arden, Brooke Astor, Andrew Carnegie, and the cemetery’s most popular interment, Washington Irving.
11:30 a.m. Next door is Old Dutch Church and Burying Grounds (430 N Broadway), the fabled haunt of the Headless Horseman and the resting place of residents thought to have inspired the characters in Irving’s “The Legend of Sleepy Hollow.” If it’s open, pop into still-functioning Old Dutch Church, a National Historic Landmark, to admire its 17th-century Dutch Colonial interior.
Noon Head to Bridge View Tavern (226 Beekman Ave) for a leisurely lunch in the beer garden. Pair any of the impressive craft beers on draft — Hill Farmstead, Equilibrium, Finback, Mikkeller, and more — with wings, burgers, or our favorite disco fries, loaded with wild-boar-chorizo chili, cheese, and pickled jalapeños.
1:30 p.m. Arrive early for a can’t-miss guided tour of Kykuit (381 N Broadway), the Rockefeller’s opulent estate. The three-hour Grand Tour meanders through the century-old house and Coach Barn, spending extra time in the landscaped gardens and art galleries, which feature a museum-quality collection of works by Picasso, Warhol, Chagall, Alexander Calder, and more. The visitor’s center is also the launch point for tours of Philipsburg Manor, an 18th-century home and gristmill, which emphasizes the role of the family’s 23 slaves, though some areas are currently closed for renovation.
5 p.m. Meet at Kingsland Point Park for Hudson River Recreation’s (299 Palmer Ave) popular Sleepy Hollow sunset tour. The guided group excursion, which includes all equipment, paddles past Tarrytown Lighthouse with golden-hour views of the Cuomo Bridge, Palisades, and NYC skyline. (Available seasonally May through October.)
7:45 p.m. Nab a waterfront table by the RiverWalk at Hudson Farmer & the Fish (11 River St), where chef-owner Michael Kaphan sources the freshest seafood and harvests seasonal produce from his other restaurant-farm, Purdy’s Farmer & the Fish in North Salem. Order a bottle of white, anything and everything from the raw bar, some salads, and a thin-crust white-clam pizza, and you’re set for the rest of the night.