Our most recommended things to do in Sleepy Hollow

Sleepy Hollow: Washington Irving Self-Guided Audio Drive

1. Sleepy Hollow: Washington Irving Self-Guided Audio Drive

Washington Irving immortalized the legendary towns of Sleepy Hollow and Tarrytown in his 1820s short story The Legend of Sleepy Hollow. On this driving tour, you’ll chase down the ghostly and headless figure on horseback from the story, while you take in the iconic and haunted sites that inspired it. Our drive starts outside Philipsburg Manor where you’ll hear how the famed author mixed Sleepy Hollow lore, local characters, and material he collected, borrowed, and stole from a range of sources to create the legend of the Headless Horseman. From there, I’ll show you the mill where a young Irving first heard the tale of a Hessian soldier who lost his head during the American Revolution. It was here, too, that the galloping goblin later raced and, using his detached head, brained schoolmaster Ichabod Crane. You’ll hear stories about the many spirits that are still believed to inhabit the town and its neighbor, Tarrytown, before ending at the site where the soldier is said to have lost his head! On this driving tour through the Hudson River Valley, you’ll also: • Find out what the 1685 Old Dutch Reformed Church graveyard has to do with the Headless Horseman • See Sleepy Hollow Cemetery where Washington Irving is buried, and hear the ghostly tale of the Bronze Lady • Pass through the often eerie roadways of Sleepy Hollow Country Club which are known stomping grounds for the galloping goblin • Cruise by Sparta Cemetery which was scarred by British cannons during the American Revolution and now is haunted by the mysterious “Leatherman” • Find out about the British spy, Major John Andre, who haunts Tarrytown’s Patriot’s Park • Hear heart-breaking tales about the three Wailing Women whose cries penetrate storms • Discover the other legend of Sleepy Hollow, Mother Hulda • Take in the historical site of the author’s former home, Washington Irving’s Sunnyside • Learn the name of the headless soldier that inspired countless iterations Join me, Jonathan Kruk, Historic Hudson Valley’s “best storyteller”, as I show you the area’s most haunted spots. I’ve performed “the Legend” a thousand times in the last twenty-five years and look forward to bringing Irving’s stories to life on this tour. By the end of this hour-long tour, you too will be under Sleepy Hollow’s spell!

From Westchester: NYC Helicopter Piloting Experience

2. From Westchester: NYC Helicopter Piloting Experience

Your first helicopter flight lesson begins with 30 minutes of ground instruction that covers helicopter flight controls, flying techniques, and safety procedures. You will then be able to join a professional flight instructor for an exciting 30-minute flight departing from Westchester County Airport in White Plains, just outside New York City. Bring a friend or family member along for the ride if you like. Once airborne, you will have the opportunity to take control of a Robinson R44 helicopter, one of the most popular civilian helicopters in the world. Take in stunning views of Westchester County, the New York/Connecticut coastline, the Hudson River, and the NYC skyline in the distance. No prior flight training or flying experience is necessary. Please note that flight lessons do not go over NYC. Flights depart from Westchester County Airport in White Plains, New York, a relaxed, crowd-free location just outside NYC. It’s easily accessed by public transit, Metro-North rail, and by car with free parking available.

Private Fall Foliage Helicopter Tour of the Hudson Valley

3. Private Fall Foliage Helicopter Tour of the Hudson Valley

Travelers get a taste of the legendary New England fall aboard this private helicopter tour over the Hudson Valley.  Marvel at the cascade of blazing reds, yellows, and oranges like a bird from the comfort of your own helicopter. Tours depart and arrive at Westchester County Airport, just outside New York City, and fly over historic landmarks all dressed in stunning colors. These include White Plains, Castle-on-Hudson, Kykuit (Rockefeller Mansion), Lyndhurst Mansion, Sleepy Hollow, Tarrytown Lighthouse, Tappan Zee Bridge, the Hudson River, Sing Sing Prison, Bear Mountain and Bear Mountain Bridge, Harriman State Park, and West Point Academy. Live tour narration by friendly and experienced pilots will make you feel comfortable and safe. Convenient roundtrip transfers are available from anywhere in Manhattan for an additional fee (if option selected). Rates are based on regular cars.

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