Rip is a descendant of a prominent Dutch family who lives in an Appalachian mountain village. He is beloved by the townspeople and children but suffers from an absolute aversion to profitable labor. He prefers running errands for others, hunting, and gossiping at the local tavern over maintaining his own farm.

Dame Van Winkle is a fierce woman who expects her husband to be a productive member of society. She strictly manages her household, keeping it in good order, and frequently harasses Rip over the worsening condition of their farm. Her temper makes the home environment highly stressful for both her husband and his dog.

Hendrick Hudson is the legendary explorer who first navigated the nearby river valley. Within the folklore of the mountains, he and his crew exist as grave figures dressed in Old Dutch clothing. They play a booming game of ninepins in a hidden mountain amphitheater.

Diedrich is a fictional historian of Dutch culture in New York. Though academic experts often doubt the factual accuracy of his research, his localized histories and folklore records are deeply beloved by ordinary people. He relies heavily on first-person accounts and local myths rather than empirical data.

Geoffrey is a collector of sketches and tales who presents the narrative to the reader. He acts as the outermost framing device of the story, serving as the custodian of Diedrich Knickerbocker's posthumous papers.

Nicholas is the patriarch of the village and the owner of the local inn. He spends his afternoons sitting in the shade outside his establishment, silently smoking his pipe and listening to town gossip.

Derrick is the village schoolmaster. He frequently joins the other men at the local inn, where he takes on the role of reciting out-of-date news from old newspapers to the captive audience.

Wolf is Rip Van Winkle's faithful pet dog. Like his master, Wolf is frequently the target of Dame Van Winkle's anger, making him just as eager to escape the house and roam the mountains.

Judith is the daughter of Rip and Dame Van Winkle. She grows up in a chaotic household with a largely absent father and a highly stressed mother.

Peter is an older resident of the village and a descendant of its original historians. He possesses unique knowledge about the area's supernatural occurrences and the legendary explorers of the Kaatskills.