Rip van Winkle is fond of wandering the countryside and wilderness with his gun or his fishing rod and can disappear for hours and hours at a time following these pursuits. He enjoys helps neighboring women with small chores and is popular with children. He also likes loitering on the bench in front of the village inn, under the picture of King George III. At the inn, he and his friends read old newspapers and discuss political events that have already occurred, drowsing away many an afternoon.
All of the activities Rip enjoys characterize him as a type: the lackadaisical colonial subject who lacks ambition, drive, and purpose. He is happy-go-lucky, and complacent, and he fails to build a future for himself or his family. He is a contrast, as he finds to his surprise after sleeping for twenty years, to the energetic new man unleashed by the American Revolution.