Rip Van Winkle details a man’s escape through the wilderness, encountering mysterious presences as he wakes up 20 years to find a new world and many changes to his own life. There have been many stories in which the wilderness acts a figurative and sometimes literal portal to the supernatural that changes the characters in a unusual and at times scary way. One story that comes to mind, is the “Young Goodman Brown:” by Nathaniel Hawthorne. It details good matured and well loved man just like Rip Van Winkle, who descents into the woods as a escort to a mysterious old man. As his journey goes the character Goodman Brown sees things that questions his very faith and love in humanity. He emerges out of the woods a changed man with a darker view of life that also affected his relationship with his loved ones. The concept of the wilderness hold supernatural ideals, said to be where all forces come to roam. Rip Van Winkle finds out that the old men in the woods were ghosts of Henry Hudson’s crew who vanished. Similarly in Young Goodman Brown, the main character encounters many anomalies that tricked his mind, such as seeing his wife and townspeople in a satanic ritual, without the idea of whether it was real or not. After their journeys through the wilderness, their own personal perception on life changed because of what they experience and the way it affected their loved ones interact with them. Rip emerged embracing life and its shortcomings, though Goodman Brown emerged with the darkness and lack of faith consuming him that he isolates himself and abuse the love of wife and townspeople. “He assured the company that it was a fact, handed down from his ancestors the historian that the Catskills Mountains had always been haunted by strange beings”