- Rip Van Winkle – A henpecked husband with an aversion to "profitable labour"; and a meek, easygoing resident of the village who wanders off to the mountains and meets strange men playing nine-pins.
- Dame Van Winkle – Rip Van Winkle's cantankerous and nagging wife.
- Rip Van Winkle Jr. – Rip Van Winkle's ne'er-do-well son.
- Judith Gardenier – Rip Van Winkle's married daughter; she takes her father in after he returns from his sleep.
- Derrick Van Bummel – The local schoolmaster who went on to serve in the American Revolution as a flag officer and later a member of Congress.
- Nicolaus Vedder – Landlord of the local inn where menfolk congregate.
- Dominie Van Schaick – The local parson.
- Jonathan Doolittle – Owner of the Union Hotel, the establishment that replaced the village inn.
- Wolf – Van Winkle's faithful dog.
- Man carrying a keg up the mountain – The ghost of one of Henry Hudson's crew members.
- Ninepin bowlers – The ghosts of Henry Hudson's crewmen from his ship, the Half-Moon; they share their liquor with Rip Van Winkle and play a game of nine-pins.
- Brom Dutcher – Van Winkle's neighbor who went off to war while Van Winkle was sleeping.
- Old woman – Woman who identifies Van Winkle when he returns to the village after his sleep.
- Peter Vanderdonck – The oldest resident of the village, who confirms Van Winkle's identity and cites evidence indicating Van Winkle's strange tale is true.
- Mr. Gardenier – Judith Gardenier's husband, a farmer.
- Baby Rip – Infant son of Judith Gardenier and grandson of Van Winkle.
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