‘Rip Van Winkle” and ‘The Legend of Sleepy Hollow”

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Washington Irving is the author of two short stories that share a handful of differences. Both stories can be found in ‘The Sketch Book of Geoffrey Crayon” and are said to be based upon German folktale. ‘Rip Van Winkle” and ‘The Legend of Sleepy Hollow” each tell their own respective stories, that are quite different from each other, especially when it comes to the setting, theme and conflict in each. As the paper progresses the differences of these stories will be brought to light, so there can be a better understand of the elements in each story.

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The first difference that can be seen in the two stories is the setting. ‘Rip Van Winkle” is set in the Kaatkill Mountains. ‘They are a dismembered branch of the great Appalachian family and are seen away to the west of the river, swelling up to a noble height and lording it over the surrounding country, Every change of season, every change of weather, indeed every hour of the day produces some change in the magical hues and shapes of these mountains, and they are regarded by all the good wives near an far as barometers.” (Levine, p.31) This exert from the text, is very descriptive in telling about how beautiful and radiant the area is. Everything seems to be in place, and those that inhabit the area are content with their living situations. In ‘The Legend of Sleepy Hollow” the setting is much different. The overview of the area is not as perfect in the eyes of others as that of ‘Rip Van Winkle”. The text from, ‘The Legend of Sleepy Hollow” states that, ‘not far from this village, perhaps about three miles, there is a little valley, or rather lap of land among high hills, which is one of the quietest places in the whole world “ the occasional whistle of a quail or tapping of a woodpecker is almost the only sound that ever breaks in upon uniform tranquility.” (Levine, p.41) This description of the setting is not necessarily negative, but it is much less vibrant than that of the other story. It depicts the area to be very quiet, even eerie in a sense. The settings of the two stories differ, but each are fitting for the specifics of the respective events that happen throughout both stories.

The theme of the two stories have their differences as well. ‘Rip Van Winkle” has multiple themes that are recognizable to the reader. One of those being freedom, the ability to make your own decisions. After awaking from the deep sleep, Rip Van Winkle’s wife had died, which gave him much more freedom than what he had ever had due to the kind of person that she was. Change is also an important theme of this story. Before the deep sleep his town was quite small, and he was a subject of George III. When he awoke, he returned to a town that was unrecognizable to him due to the expansion and new buildings that lined the streets. He was also a citizen of America under George Washington upon his arrival, which was much different than being a subject. The theme of change repeats itself constantly in this story. Rip Van Winkle’s life was changed forever when he awoke. As an alien in his own home, he had a completely new identity and he made the best of it by telling his stories of the past to others. In ‘The Legend of Sleepy Hollow” the theme is different for the most part. The theme of marriage is quite evident throughout the whole story, which is not the same with ‘Rip Van Winkle,” in fact Rip was happy to come back to his wife being gone. Ichabod Crane and Brom Bones were both hoping to marry Katrina Van Tassel. One wanted her love in a genuine way, while the other just wanted to marry her for her father’s money. Change was somewhat talked about, but it was not what the whole story was based upon which makes the two themes differ.

Lastly the conflicts of the stories are found to be different. The story of Rip Van Winkle has a conflict of man vs. nature. Rip goes off into the woods and meets these strangely dressed men and choose to drink the concoction that they made, which resulted in his deep sleep. He woke up to new surroundings, the area around him was not the same which confused him. When he finally returned to town, he was even more confused, the text reads that, ‘strange names were over the doors, strange faces at the windows, and everything was strange. His mind now began to misgive him, that both he and the world around him had been bewitched.” (Levine, p.36) The conflict caused Rip to think that there was something wrong with him, that he was now a stranger in the place that he was most looked up to. The conflict that was experienced in ‘The Legend of Sleepy Hollow” was man vs. man instead of man vs. nature. This conflict is very easy to see due to the competition that there was between Ichabod Crane and Brom Bones due to their desires to marry the same woman. This conflict is supported by the statement from the text that reads, ‘such was the formidable rival with whom Ichabod Crane had to contend (Brom Bones) and considering all things, a stouter man than he would have shrunk from the competition and a wiser man would have despaired”. (Levine, p.49) Ichabod Crane and Brom Bones were both determined to win over Katrina and they didn’t care what stood in their way, especially each other. This was a conflict that was relevant throughout the whole story, until the choice was made. Rip Van Winkle struggles with nature and the changes that happen to the area around him in twenty years of deep sleep, while the men from sleepy hollow struggled with each other.

After reading and understanding each story they have their own unique differences in setting, theme and conflict. Although they were written by the same man, Washington Irving, he did not make the books have similar story lines or allow the only difference to be the characters. One thing that his writing did do was help to better realize the changes that were happening in America at the time. The statement, ‘Rip Van Winkle” and ‘The Legend of Sleepy Hollow” explored the social and cultural changes occurring in America at the time,” (Nilsson, 2011-12) was made in an article about short stories growing up. Both stories tell a unique tale that allows for greater learning to the reader. When comparing the two stories, the conflicts in each made all the difference in the meanings of the stories.

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'Rip Van Winkle" and 'The Legend of Sleepy Hollow". (2021, Mar 09). Retrieved June 9, 2023 , from

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