In this scene, Rip has made it to one of the highest and loneliest parts of the Catskills. It is close to evening and as Rip looks down into the mountain glen, he hears a voice calling his name. Thinking someone is in trouble, he descends into the glen. Rip is surprised by the appearance of the bearded man he sees, who is short and dressed in old-fashioned ("antique") Dutch clothing. He carries a keg of beer. Rip follows him and sees more people in old-fashioned clothes: doublets and enormous breeches, along with beards and odd faces:

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.

Their party of "pleasure" strikes Rip as "melancholy" because, although they are playing nine-pins, these people are completely solemn and silent. They stare at him as if they are statues, and the only noise he hears is the thundering sound of the bowling balls.

Irving spends so much time describing this scene because he wants to make clear that Rip has entered a liminal or magical space, where the ordinary aspects of life have changed. He wants the reader to know this is a strange or unusual area and that Rip has entered some sort of alternative reality where the everyday rules no longer apply. This raises in the reader the possibility that something unusual will happen and helps the reader accept that in this strange, enchanted place, Rip really could fall asleep for twenty years.