"Rip Van Winkle" is widely considered by critics to be a classic short story. Even at the time of publication, as part of the first group of stories in The Sketch Book of Geoffrey Crayon, Gent, it was considered a triumph of an emerging form: the short story. As the work has aged, it continues to be praised for its breezy tone, its easy humor, its inherent strangeness, and the open-ended nature of its message. Further crucial to its success is the fact that the story is easily digestible.  

Even to modern readers, “Rip Van Winkle" reads like a traditional folktale, perhaps because it was based upon one. This familiar genre along with the fanciful tropes that have become increasingly familiar to readers lend a timelessness to the narrative. Some critics have suggested that in combining the folktale and the essay-sketch, Irving created the genre of the short story as readers recognize it today. For this reason, some consider “Rip Van Winkle” the most important story written in the early days of the United States. By combining the archetypes of both the folktale and the travel narrative, the story possesses a depth neither genre might typically sustain on their own. This surprising depth allows for myriad readings of the text, which makes this tale a staple in English classes across the United States. Rip and his story act as blank canvases onto which students can project a wide variety of analyses. The enduring legacy of the story is that, for all of its brevity and seeming simplicity, the tale encourages rereading and reexamination.