The settlers of Sleepy Hollow and their descendants enjoyed the simple pleasures of life. They were superstitious, and they often loved telling tales of suspected hauntings.
The original settlers were Dutch farmers. Those settlers and their offspring had lived there ever since. The area seemed to have a "drowsy, dreamy influence" which "hung over the land." One of the stories that was told among the townspeople was that long ago, a German doctor bewitched the place. Others suggested that an Indian chief held powwows there, before the discovery of the area by Hendrick Hudson.
The superstitious descendants of the original Dutch settlers "[saw] strange sights, and [heard] music and voices in the air." The most frequently talked about ghost was the headless horseman, said to be the spirit of a Hessian soldier who lost his head to a cannonball. Women told such tales as they spun wool and roasted apples by the fire when the weather was cold. Townsfolk spent evenings by their doors, soaking in the night air.