In the tenth chapter of his book Lives and Opinions of Eminent Philosophers, the third-century AD Greek historian Diogenes Laertius relates the story of the legendary sage Epimenides of Knossos, who was said to have been a shepherd on the island of Krete. One day, Epimenides followed after a sheep that had wandered off and, after becoming tired, went into a cave under Mount Ida and fell asleep. When he awoke, he continued searching for the sheep, but could not find it, so he returned to his father's farm, only to discover that it was under new ownership. He went home, only to discover that the people there did not know him. Finally, he encountered his younger brother, who had become an old man, and learned that he had been asleep in the cave for fifty-seven years. According to the different sources that Diogenes relates, Epimenides lived to be 154, 157, or 299 years old. Multiple sources have identified the story of Epimenides as the earliest known variant of the "Rip Van Winkle" fairy tale.
In Christian tradition, there is a similar, well-known story of "The Seven Sleepers of Ephesus", which recounts a group of early Christians who hid in a cave circa 250 AD, to escape the persecution of Christians during the reign of the Roman emperor Decius. They fell into a miraculous sleep and woke some 200 years later during the reign of Theodosius II, to discover that the city and the whole Empire had become Christian. This Christian story is recounted by Islam and appears in a famous Sura of the Quran, Sura Al-Kahf. The version recalls a group of young monotheists escaping from persecution within a cave and emerging hundreds of years later.
The story of "Rip Van Winkle" itself is widely thought to have been based on Johann Karl Christoph Nachtigal's German folktale "Peter Klaus", which is a shorter story set in a German village. It tells of a goatherd named Peter Klaus who goes looking for a lost goat. He finds some men drinking in the woods and, after drinking some of their wine, he falls asleep. When he wakes back up, twenty years have passed.
In many ways, the story is a classic European faerie tale of a man who is actually rewarded for helping the faeries move their barrel. They advance him to a time in life where he is free of his nagging wife and is now old enough for it be respectable for him to take it easy and play with children, working when he wants to instead of when he has to, supported by his loving, grown children. The theme of independence is also explored; the young Van Winkle lives in British America and is a subject of the King; the old Van Winkle awakes in a country independent of the Crown. On a personal level, the awakened Van Winkle has gained another form of "independence": being widowered from his shrewish wife.
In Orkney, there is a similar folktale linked to the burial mound of Salt Knowe, adjacent to the Ring of Brodgar. A drunken fiddler on his way home hears music from the mound. He finds a way in and finds the trowes (trolls) having a party. He stays and plays for two hours, then makes his way home to Stenness, where he discovers 50 years have passed. The Orkney Rangers believe this may be one source for Washington Irving's tale because his father was an Orcadian from the island of Shapinsay and would almost certainly have known the story.
In Ireland, the story of Niamh and Oisin has a similar theme. Oisin falls in love with the beautiful Niamh and leaves with her on her snow white horse, bound for Tir Na nOg – the land of the ever-young. Missing his family and friends, he asks to pay them a visit. Niamh lends him her horse, warning him never to dismount, and he travels back to Ireland. But 300 years have passed; his family and fellow warriors are all dead. When Oisin encounters some men trying to move a boulder, he reaches down to help them, the girth of the horse's saddle snaps, and he falls to the ground. Before the watching eyes of the men, he becomes a very, very old man.
Author Joe Gioia suggests the basic plot strongly resembles, and may have originated with, an upstate New York Seneca legend of a young squirrel hunter who encounters the mystic "Little People", and after a night with them returns to his village to find it overgrown by forest and everyone gone: that single night had lasted a year.
The story is also similar to the ancient Jewish Talmudic story about Honi the Circle-Maker (Honi M'agel), who falls asleep after asking a man why he is planting a carob tree which traditionally takes 70 years to mature, making it virtually impossible to ever benefit from the tree's fruit. After this exchange, Honi falls asleep on the ground, is miraculously covered by a rock, and remains out of sight for 70 years. When he awakens, he finds a fully mature tree and learns he has a grandson. When nobody believes that he is Honi, he prays to God, and God takes him from this world.
The story also bears some similarities to stories from east Asia, including the third century AD Chinese tale of "Ranka", as retold by Lionel Giles in A Gallery of Chinese Immortals, and the eighth-century Japanese tale "Urashima Tarō". The Hindu story of Muchukunda from the Bhagavatam also displays many similarities to the story of "Rip Van Winkle".