
Destination guide
Sleepy Hollow: The Village That Voted for Its Own Legend
Plan the Sleepy Hollow stop. This guide does not cover the New York City or Montauk legs.
Read the free guide →Optional premium expansion available.

New York, United States
Two days across New York State: from the Hudson Valley village that gave America its Headless Horseman, south into Manhattan to a windowless AT&T switching tower that The Intercept tied to NSA surveillance in 2016, and out to the tip of Long Island where a decommissioned Cold War base is rumored to have hidden a government mind-control program.
"The Legend of Sleepy Hollow" appeared in 1820 as the sixth number of Washington Irving's The Sketch Book, presented as papers found after the death of a fictional Diedrich Knickerbocker, and it never names the church that visitors now connect with it. Irving is buried in Sleepy Hollow Cemetery nearby, under his third headstone. On December 10, 1996, the village of North Tarrytown voted 1,304 to 710 to rename itself Sleepy Hollow.
Start in the Hudson Valley village Washington Irving made famous in 1820. Walk the Old Dutch Burying Ground and the bridge his Headless Horseman is said to have chased Ichabod Crane across.
A windowless, 550-foot AT&T switching building in Manhattan. In 2016, The Intercept reported, drawing on Edward Snowden's leaked documents, that it appears to house a major NSA surveillance hub.
Drive south into Manhattan to look up at a windowless 550-foot tower on a Tribeca street corner. John Carl Warnecke & Associates designed it as a long-distance telephone switching center, completed in 1974 and still used by AT&T. In 2016, The Intercept, drawing on Edward Snowden's leaked NSA documents, reported that the building appears to be an NSA surveillance site code-named Titanpointe.
A Cold War radar station on the eastern tip of Long Island, decommissioned and handed to the state as a park. A 1992 book turned its sealed concrete into claims of mind control and time travel, and a Netflix series was pitched under its name.
Finish at the eastern tip of Long Island, where a decommissioned Cold War radar station is now a public state park, and, according to a persistent conspiracy theory, was once the site of secret government experiments in time travel and mind control.
Share current access details or a useful observation for the next explorer.
No route notes yet. First to drive it, first to report back.