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How to Spend a Perfect Saturday in Sleepy Hollow

Enjoy a Saturday in Sleepy Hollow | Adobe Stock | lspi138

Visitors flock to this Hudson River-facing village for gorgeous foliage, Halloween events, and to celebrate Washington Irving.

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. So, pack your bags and enjoy your Saturday in Sleepy Hollow.

By Samantha Garbarini & Anthony Tornatore

10 a.m. – Grab Something Sweet from Los Andres Bakery

Grab a quick bite at Los Andes Bakery (180 Valley St.; 914.631.3256). 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.


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11 a.m. – Head to the Sleepy Hollow Cemetery

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; 914.631.0081). 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.


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12 p.m. – Have Lunch at the Bridgeview Tavern

Head to Bridge View Tavern (226 Beekman Ave.; 914.332.0078) 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.


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2 p.m. – See Where the Headless Horseman Haunts

Back towards the Sleepy Hollow Cemetery is the 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.


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4 p.m. – Take a Sunset Kayak Tour

Meet at Kingsland Point Park for Hudson River Recreation’s (Riverwalk Center; 914.682.5135) 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)

6 p.m. – Enjoy Dinner at Hudson Farmer & the Fish

Nab a waterfront table by the RiverWalk at Hudson Farmer & the Fish (11 River St.; 914.631.8380), 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.

8 p.m. – Stock Up on Sweets at Sweet Ambateño Bakery

Before you head to your room for the night, make sure to stop by Sweet Ambateño Bakery (173 Cortlandt St.; 914.909.2473) for savory sweets and desserts to die for. This Ecuadorian bakery has all kinds of delicious cakes, bread, cookies, and other amazing treats. Make sure to try the flan and thank us later.

9 p.m. – Rest at the Tarrytown House Estate on The Hudson

Located a few miles north of Dobbs Ferry, this 4-star hotel embodies elegance reminiscent of America’s Gilded Age. Overlooking the Hudson River, the Tarrytown House Estate (49 E Sunnyside Ln; 914.591.8200) is a haven for recreation and relaxation. Hit the tennis court, shoot some hoops, or take a dip in the pool. When you are done with that, enjoy a fantastic meal at Goosefeather, one of 2020s top 20 restaurants in the USA by Esquire Magazine.

Related: Top 3 Spooky Spots In Yonkers


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