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One day in Sleepy Hollow, New York

Don’t lose your head, pumpkin — here are the top spots to explore when visiting the Sleepy Hollow area.

A small stone church located among many aging gravestones in a cemetery.

Sleepy Hollow cemetery offers a wealth of history, from massive mausoleums to scenes from Washington Irving’s famous legend.

Photo by BOStoday Team

Salem isn’t the only city that’s ripe for fall day trips. If witchcraft isn’t your bailiwick, take the roughly four-hour car ride to Sleepy Hollow, the idyllic New York home of breathtaking architecture, cemeteries, and Washington Irving’s infamous short story.

Whether you’re seeking out real scenes from “The Legend of Sleepy Hollow” or a fulfilling autumn road trip, this area is a gem bursting with foliage and American history.

If you’re headed to the Sleepy Hollow area, here are a few must-see stops.

🪦 Sleepy Hollow Cemetery, 540 N. Broadway, Sleepy Hollow
The Headless Horseman’s main haunt is this sprawling garden cemetery, teeming with the graves of notable figures (like Washington Irving himself) and ornate family mausoleums for local big wigs such as the Rockefellers and Chryslers. Daytime and lantern tours explore different aspects of the cemetery’s history, from the “American Artistocrats” edition, to a walk focused solely on Irving and his influence. As you stroll through the grassy acres, make sure to find the Old Dutch Church, which is mentioned in the legend. Pro tip: The Headless Horseman Bridge is nearby at 415 N. Broadway — look for the historic site marker.

📚 Washington Irving’s Sunnyside, 3 W. Sunnyside Ln., Irvington
Walk through the vine-covered home of the author — complete with much of the original 19th century furnishings — and learn about his life along the Hudson River from staff in historically-accurate garb.

🏰 Lyndhurst Mansion, 635 S. Broadway, Tarrytown
“Castle” might be a better descriptor than “mansion” for this breathtaking property from the 1800s. Go full Gothic at this historic estate, which was once used as the setting for the 1970s “Dark Shadows” films and on HBO’s “The Gilded Age.” Choose between tours focused on the mansion’s basic layout, grounds, and unique spaces like the observation tower + bowling alley.

Bonus: Enjoy Mediterranean cuisine for brunch or dinner at Mint Premium Foods, or grab some no-fuss American fare at Bella’s Restaurant.

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