This creative nonfiction work focuses on stories surrounding forgotten monuments in the Berkshire region of western Massachusetts. The Berkshires have long had a distinct regional culture that has set them apart from the rest of Massachusetts and indeed from the rest of the rural and urban United States. As one of the first American frontiers, the region was settled by self-reliant and determined pioneers who had to endure harsh environments, Native American unrest, wars, and political and religious disturbances and disagreements. No other landscape can boast the attentions of literary giants like Herman Melville and Nathaniel Hawthorne, while also showcasing the artistic work of residents like Norman Rockwell. Even the natural landscape poses a contrast to the rest of Massachusetts. While Massachusetts is relatively flat, the Berkshires are a land of mountain ranges, including both the Berkshire mountains in the east, really the southern branch of the Hoosac Range, and the Taconic Mountains in the west. To tell the story of the Berkshires, this work focuses on four sites: the Hancock Shaker Village in Hancock, Monument Mountain in Great Barrington, the Hudson and Chester Granite Quarry in Becket, and the Garnet Peak plane crash monument in Peru. Each of these areas is described firsthand as they exist in the present day through descriptions of hikes that serve to take the reader into the very woods where these stories took place. Then, the history of each area was analytically explored using historical texts, which are used to provide the historical context of the Berkshires. From the history of the Berkshires, greater conclusions can be drawn about the United States as a country of progress, innovation, and hope.