Irving describes his main character as an amiable fool. As stated in the text Van Winkle is ".one of those happy mortals, of foolish, well-oiled dispositions, who take the world easy, eat white bread or brown, which ever can be got with least thought or trouble, and would rather starve on a penny than work for a pound." He is also said to be a man who, "If left to himself would whistle is life away." Clearly Van Winkle has concern for the matters of getting ahead. Yet one has to look at how he fits into his rustic community to get a clearer impression of him. .
Although much satire is made of Van Winkle being a "henpecked husband", the story also gives evidence of his many good works. Unafraid of hard labor, Van Winkle is seen by those of his community as one who, "would never even refuse to assist a neighbor in the roughest of toil, and was a foremost man at all country frolics for husking Indian corn, or building stone fences." He is also seen as one well liked by the "gentler sex", as the text continues, "The women of he village too, used to employ him to run their errands and to do such little jobs as their obliging husbands would not do for them." He also has his place amongst the idle philosophers who gather in front of the inn, to discuss the events of the day. In this instance Van Winkle finds himself in good company: Nicholas Vedder is the owner of the Inn and Van Bummel is the town's school teacher. Even the children of the village adore him. The reason for his popularity gives further evidence to Van Winkle's character. "He assisted at their sports, made their playthings, taught them to fly kites and shoot marbles and told them long stories of ghosts, witches and Indians." In view of all this Van Winkle appears to epitomize Christian Charity and kindness. His only real flaw is that he would rather, ".attend to anybody's business but his own." But constant attention to others means disaster at home, and Van Winkle is a failure with both his farm and his wife.