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How to Spend a Perfectly Spooky Saturday in Sleepy Hollow

It's that time of year when visitors flock to the riverfront village for gorgeous foliage and superb Halloween events in Westchester.

Sleepy Hollow Cemetery
Sleepy Hollow Cemetery. Photo by Sabrina Sucato

In October, visitors flock to this Hudson River-facing village for gorgeous foliage, Halloween events, and a celebration of Washington Irving’s famous literary work, “The Legend of Sleepy Hollow.” Whether you’re looking for a lantern tour, a journey through a historic estate, or just a spooky hayride, this is the Halloween town for you. What’s more, these events paired with meals from some of the village’s top eateries are a match made in heaven. So, pack your bags and enjoy your Saturday in Sleepy Hollow.

9 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, a.k.a. buttery cookies held together by a layer of dulce de leche.

10 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 the 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. Or you can sign up for a guided tour of the cemetery.

11 a.m. – See where the Headless Horseman haunts Sleepy Hollow

Near 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 the still-functioning Old Dutch Church, a National Historic Landmark, to admire its 17th-century Dutch Colonial interior.

12 p.m. – Have lunch at Bridgeview Tavern

Head to Bridgeview Tavern (226 Beekman Ave.; 914.332.0078) for a leisurely lunch in the beer garden. Pair any of the restaurant’s craft beers or ciders on draft — Hill Farmstead, Hudson Valley Pink Lemonade Silhouette, Hudson North Standard, Maine Fall, and more — with wings, burgers, or our favorite “Disco Is Dead” fries, the latter which come loaded with wild-boar-chorizo chili, cheese, pickled jalapeños, and bacon.

2 p.m. – Take a tour of Philipsburg Manor 

Across the street from the Sleepy Hollow Cemetery sits Philipsburg Manor (381 N Broadway; 914.366.6900), a mill and trading complex where an enslaved community lived and labored for generations. Guided tours of the manor last about an hour and 40 minutes and run from 10 a.m. to 4 p.m.

4 p.m. – Check out the Tarrytown Lighthouse in Sleepy Hollow

The Tarrytown Lighthouse in Sleepy Hollow was built in the 1880s and lies right along the Hudson River, making it the perfect spot for a pre-dinner stroll. Along the RiverWalk, you can catch picturesque views of the Governor Mario M. Cuomo Bridge as it sits behind the lighthouse, making it an ideal Instagrammable spot. There’s metered parking on Beekman Avenue and paid parking in Kingsland Point Park.

5 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 mushroom pizza, and you’re set for the rest of the night.

7:30 p.m. – Experience “The Legend of Sleepy Hollow” like never before 

After you fill up on much-needed grub, go back in time to the 1800s with this immersive experience. Master storyteller Jonathan Kruk will perform outdoors under the stars just up the road from Sleepy Hollow at Washington Irving’s Sunnyside estate in Irvington. Kruk will put on a dramatic performance of the classic tale with live music and sound effects by Jim Keyes. There will even be an appearance from the Headless Horseman.

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

Located a few minutes from Sleepy Hollow, this four-star hotel embodies elegance reminiscent of America’s Gilded Age. Overlooking the Hudson River, 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. If the hunger pangs hit, order a fantastic meal at Goosefeather, where you can enjoy modern, seasonal Chinese fare made by Chef Dale Talde.

Related: 6 Westchester Cemeteries Filled With Beauty and History

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