Coming October 19, 2013. Get in the Halloween spirit with the Sleepy Hollow Halloween 10K race! A fun, timed race through the streets of historic Sleepy Hollow, New York. The well-marked route travels within view of the Headless Horseman Bridge, Sleepy Hollow Cemetery and the Old Dutch Church. Just for kicks, dress up like Ichabod Crane or the Headless Horseman!