Ichabod is a tall and physically awkward schoolteacher from Connecticut who relocates to the Dutch settlement of Sleepy Hollow. He instructs the male children of local farmers in a one-room schoolhouse and provides psalm-singing lessons to women in the village. He possesses an enormous appetite and constantly seeks invitations to home-cooked meals. His highly superstitious nature makes him an avid consumer of local ghost stories and books about witchcraft.

Brom is a burly equestrian who serves as the primary local rival for Katrina's affection. He possesses immense physical strength and maintains a mischievous personality. Because his competitor avoids direct confrontation, Brom resorts to practical jokes and schoolhouse vandalism rather than physical fights. He openly mocks local superstitions and boasts about his nighttime encounters in the woods.

Katrina is the eighteen-year-old daughter of Sleepy Hollow's wealthiest farmer. She wears clothing that mixes ancient and modern fashions to highlight her physical attractiveness. She enjoys the attention of multiple suitors and actively entertains different men. She participates in local social events and takes weekly singing lessons.

Baltus is a prosperous Dutch farmer who owns a highly productive property situated near the Hudson River. He provides a comfortable and abundant life for his family through his agricultural success. He hosts a sumptuous autumn gathering featuring music, dancing, and large quantities of food. He remains content with his rural life and welcomes visitors to his estate.

The Headless Horseman is a ghostly figure believed to be the spirit of a Hessian soldier who lost his head to a cannonball during the Revolutionary War. He rides a black horse through the valley at night and returns to the church graveyard by morning. He serves as the primary source of terror for Sleepy Hollow residents and features prominently in local storytelling.

Dietrich is a fictional Dutch historian who narrates the events occurring in Sleepy Hollow. He states he visited the region during his youth and bases his account on local hearsay. His reliance on second-hand information shapes the recounting of the area's supernatural events.

Hans is a farmer living in the agricultural community of Sleepy Hollow. He evaluates the local school system and questions the practical value of formal education for agricultural families. He represents the traditional mindset of the local Dutch settlers.

Daredevil is a fast and capable horse owned by a prominent local equestrian. He participates in his owner's wild rides through the countryside. He features prominently in a story about racing a ghostly figure through the forest.