Big Indian is tied to the legend of Winnisook, an 18th century Munsee of the Lenape Nation in Ulster County who was said to be over seven feet tall and whose story was likely embellished over time, though surveys from 1786 confirm that Big Indian was already recorded as a place name. According to the legend, Winnisook lived in the Marbletown area, fell in love with Gertrude Molyneaux, and after her unhappy marriage to Joseph Bundy, she eloped with Winnisook and had several children with him. Years later, after Winnisook led a livestock raid against Dutch farmers, a posse including Bundy pursued him, and Bundy allegedly killed him in the area now called Big Indian. One version holds that Gertrude then moved her family to the area to be near Winnisook's grave, and old land title records in the Lost Clove valley carry her family name. The region also includes the site of Aley's General Store, later known as Morra's Market, which many believe served as a stop on the Underground Railroad in the 1800s. Early local industries included logging, lumber milling, and furniture making, which supported the construction and furnishing of inns, boarding houses, and summer resorts. Oliverea's Winnisook Club, founded in 1886 at the base of Slide Mountain, built a lodge in 1887 on 1,600 acres and later added 14 private homes; Winnisook Lake there was dammed into a five-acre recreational lake and is the highest lake in the Catskills. Visitors to the club included William Jennings Bryan and John Burroughs. The original building later associated with Rudy's Big Indian and the Jake Moon Restaurant was built by Jake Moon, a part Native American railroad yard guard who survived a landslide in the 214 notch between Chichester and Phoenicia and then settled his family there; in 1994 his great-great-great grandson Daniel E. Smith became owner and manager, and the expanded building is now the Peekamoose Restaurant on Route 28 and Lasher Road.