Ichabod Crane is an outsider in Sleepy Hollow, although he does manage to ingratiate himself with many of the women of the valley by gossiping with them and serving as a babysitter. As a schoolmaster, he is a strict disciplinarian but probably not a very effective teacher. His level of intellectual sophistication is questionable, given that his favorite author is the Puritan Cotton Mather, who painted the world in very black-and-white terms, and the fact that he believes every ghost story he ever hears. He is so filled with fear as a result of believing those stories that he appears truly cowardly on most nights. Ichabod is awkward and odd looking, and his greed and misplaced high self-esteem make him even more unattractive. He truly believes he is something of a "ladies' man" and is capable of winning the heart of the valley's most eligible young woman, Katrina Van Tassel. He thinks his horrible singing voice is good, and he believes his jerky dancing is the best around. It is telling that no one in Sleepy Hollow really misses Ichabod Crane when he is gone, not as a teacher or a man.
Katrina Van Tassel
Katrina Van Tassel is the star of her own life story, the equivalent of a modern-day movie star in her small town. She can do whatever she wants, and one way she amuses herself is by leading on various men who desire her. The most hapless of her victims is Ichabod Crane, whom she seems to lead on and then coldly toss aside just when he thinks he has won her. No doubt Katrina's plan all along has been to join her life with her male equal, the hero of Sleepy Hollow, Brom Bones. It's no surprise to learn at the end of the story that they have wed.
Brom Bones is a combination of a modern-day male model, famous athlete, and all-American boy next door. He is good-looking and fun-loving. He is revered by people his own age and the older generations as well. Brom and his gang pull plenty of pranks, but they don't really mean much harm by them. However, when he has had enough of Ichabod Crane and his pursuit of Katrina Van Tassel, Brom most likely pulls off the biggest prank of all—posing as the Headless Horseman and scaring Ichabod into running away from Sleepy Hollow forever.
Baltus Van Tassel
Baltus Van Tassel is the epitome of a contented man. He is wealthy and comfortable. He has a loyal and happy wife, and he adores his only child, Katrina. Van Tassel enjoys the camaraderie and respect of the valley residents. He appears to be generous in sharing his abundance and enjoys providing hospitality to all. No doubt he is proud when Katrina chooses to marry the finest young man in the valley, Brom Bones, especially since Baltus has little desire to leave the confines of his happy community.
Readers learn about the Headless Horseman from the many different versions of the tale told about him. He is supposedly the ghost of a Hessian soldier who had his head shot off by a cannonball in the Revolutionary War and constantly seeks the missing body part. The night the shunned Ichabod Crane leaves the Van Tassel party, readers are given a glimpse of a headless rider, who carries his head on the saddle in front of him as he shadows and then pursues the terrified Ichabod Crane. But is that horseman really Brom Bones in disguise, and is that head really a pumpkin?