One of Irving's specialties was his descriptiveness. In The Legend of Sleepy Hollow, his descriptions of the characters and landscape are so meticulous that it all seems real even today. Of course as we know from class Irving was able to accomplish this because he drew his inspiration from real places and people as well as other American Literature. The characters for this story came from the experiences he had before he started writing. The names were Dutch-named characters that stemmed from the huge Dutch influence in the New York area. The character of Ichabod Crane was based on the stereotypes of the American Yankee. Also there are some speculations that Ichabod was inspired by a man who taught in a schoolhouse where Irving lived back in 1809. And one of the most obvious descriptions is the town of Sleepy Hollow. Sleepy Hollow was a real town close to Tarrytown, New York. He used real land markers and vivid descriptions of the burial ground that was actually in that town. http://www.helium.com/items/1176639-the-inspiration-of-the-legend-of-sleepy-hollow-by-washington-irving
While I was searching for information I stumbled upon this video on YouTube, someone actually retraced the chase of the headless horseman through Sleepy Hallow on horseback... Enjoy
http://www.youtube.com/watch?v=P_iP5iQWeUE&feature=player_embedded#!