One key element of Romanticism in "Rip Van Winkle" is the supernatural. Along with appreciating nature, Romantic writers pushed back against Enlightenment rationalism; they felt that it was a disservice to cut out the wit and wisdom inherent in whimsy and fairytale. For example, Coleridge (a seminal Romantic poet) wrote about the supernatural in poems such as The Rime of the Ancient Mariner.

The "Rip Van Winkle" plot pivots on supernatural elements. We are asked to suspend our disbelief (one of Coleridge's ideas!) and accept that Rip stumbles into a liminal space while on one of his walks in the Catskills. It is in this space where Rip encounters supernatural people (perhaps the ghosts of early Dutch settlers), who give him a drink that puts him to sleep for twenty years. Accepting this fantastic plot point is essential to understanding Washington Irving's story.

Irving's description of the liminal "deep mountain glen"—scarcely lit with the rays of the setting sun—and the people Rip meets there is the most image-rich section of the story, showing a Romantic fascination with the wonder and poetry of the supernatural:

They were dressed in a quaint, outlandish fashion; some wore short doublets, others jerkins, with long knives in their belts, and most of them had enormous breeches, of similar style with that of the guide's. Their visages, too, were peculiar: one had a large head, broad face, and small, piggish eyes; the face of another seemed to consist entirely of nose, and was surmounted by a white sugar-loaf hat, set off with a little red cock's tail. They all had beards, of various shapes and colors.

Through the device of Rip's long sleep, Irving is able to document the many changes that occur in America during a twenty-year span.

One central aspect that you need to focus on is the way that nature is treated in this excellent short story. Apart from the elements of the supernatural and the other aspectscommon to Romanticism, there is a definite theme of the natural world in this story. Rip van Winkle's "escape" from the crowded city into nature, where he experiences a massive life change, is a recurrent motif in Romanticism. It is the domestic strife that Rip suffers that drives him away from the town, the symbol of civilisation and stress, and into the woods, which Rip seems to do quite a bit. He clearly experiences peace and relief whilst "in nature" and contemplating its beauty:

From an opening between the trees he could overlook all the lower country for many a mile of rich woodland. He saw at a distance the lordly Hudson, far, far below him, moving on its silent but majestic course, with the reflection of a purple cloud or the sail of a lagging bark here and there sleeping on its glassy bosom, and at last losing itself in the blue highlands.

It is of course whilst in nature that Rip is called into the "wild, lonely and shagged" mountain glen where he experiences his prolonged sleep and repose, emerging into a very different world. Thus, the beauty of nature and how it provides succour to the soul, overwhelmed by the stresses and strains of life in the city, are key elements in Romantic fiction and this aspect is certainly to be found in this great short story.