The journeys of Young Goodman Brown and Rip Van Winkle are similar, first, in that they each embark alone but meet up with companions and, second, in that they both have a supernatural experience. They are different in that Goodman Brown's experience on his journey is unpleasant, while Rip's is pleasant.

Brown is changed for the worse because he becomes a grim, suspicious person who can trust no one. Rip does not change, but the circumstances around him change: he experiences the liberation of his wife dying and becomes a quaint relic in a new republic. Goodman Brown faces the fact that people have evil qualities: his is a moral transformation. Rip sees a changed political landscape of robust democratic involvement in a new country that an apathetic man like him cannot appreciate.

Goodman Brown heads alone into the woods, where he encounters people he knows, like the village pastor and Goody Cloyse, who taught him Sunday School. In a clearing, a seemingly Satanic ritual is going on, and Faith, Brown's wife, is part of it. Supernatural events in the woods include an encounter with the devil, whose staff seems to turn into a wriggling snake.

Rip also heads out alone into the woods, going deep into the Catskills and finding a group of people in Dutch clothing of the seventeenth century. They offer him a supernatural beer that puts him to sleep for twenty years.

Brown is horrified by what he witnesses, which is that people he thought were pure and good turn out to have evil elements to their characters. The affable Rip, however, enjoys his time with the mysterious ancient Dutch people.

Brown is changed for the worse by his experience. As we learn at the end of the story,

when he had lived long, and was borne to his grave, a hoary corpse, followed by Faith, an aged woman, and children and grand-children, a goodly procession, besides neighbors, not a few, they carved no hopeful verse upon his tombstone; for his dying hour was gloom.

Rip himself doesn't change, but it takes some time for him to acclimate to his new environment, which has changed radically:

It was some time before he ... could be made to comprehend the strange events that had taken place during his torpor. How that there had been a revolutionary war—that the country had thrown off the yoke of old England—and that, instead of being a subject to his Majesty George the Third, he was now a free citizen of the United States. Rip, in fact, was no politician; the changes of states and empires made but little impression on him; but ... he had got his neck out of the yoke of matrimony [his wife died], and could go in and out whenever he pleased, without dreading the tyranny of Dame Van Winkle.