A wooden bridge crosses a reflective pond, leading to rustic buildings surrounded by lush greenery and flowers under a clear blue sky. Sleepy Hollow The tale of the Headless Horseman has been an integral part of the American narrative since Washington Irving penned “The Legend of Sleepy Hollow” in 1820. The quiet New York town is in some ways built upon this gothic story, and the contents of the legend live have intermeshed with the town’s actual history.