Over a deep black part of the stream, not far from the church, was formerly thrown a wooden bridge; the road that led to it, and the bridge itself, were thickly shaded by overhanging trees, which cast a gloom about it, even in the daytime; but occasioned a fearful darkness at night. Such was one of the favorite haunts of the Headless Horseman, and the place where he was most frequently encountered.

In this quote, which occurs before Ichabod’s climactic ride from the Van Tassels’ party, the narrator blends the natural with the supernatural in setting the scene for a story of Sleep Hollow’s most infamous apparition. Here, the narrator steeps descriptions of nature with darkness and dreariness to make them effectively distressing. The quote suggests that places where nature is inky, thick, untamed, and suffocating are bound to attract supernatural entities such as the spectral Headless Horseman.

As Ichabod approached this fearful tree, he began to whistle; he thought his whistle was answered; it was but a blast sweeping sharply through the dry branches. … Suddenly he heard a groan—his teeth chattered, and his knees smote against the saddle: it was but the rubbing of one huge bough upon another, as they were swayed about by the breeze. He passed the tree in safety, but new perils lay before him.

During Ichabod’s ride from the Van Tassel party, the narrator humorously reveals how nature stokes Ichabod’s frightful imagination of supernatural haunts in the dark. As Ichabod nears the hulking tulip tree with a fearsome history, his nerves create a formidable aural experience as breezes become taunting whistles and rubbing tree boughs resounding groans. Though the narrator speaks in jest about Ichabod’s fear of his surroundings, the noises of nature foreshadow Ichabod’s fateful encounter with the Headless Horseman.