Sleepy Hollow The horsemans head still lies somewhere on the battlefield, the people of Sleepy Hollow said. Every night, he rides back to the battlefield to look for it. One dark night, Ichabod Crane - the village schoolmaster - saw the Headless Horseman. Or did he? Rip Van Winkle Rip Van Winkle did not like working on his farm and his wife was always angry with him. He wanted to forget his troubles for a day. So he took his dog and his gun and he walked up into the Catskill Mountains.