The Dempsey Massengale Jr. family lived on this ridgetop just south of present-day Rugby from the 1860s to the early 1900s, on a terrace farmstead beside the historic trace later called Allerton Road, with fields, pastures, orchards, and woodlands stretching down the ridge and outbuildings such as a smokehouse, chicken house, corn crib, stock pens, and equipment shed. The visible stone chimney remains are the only standing evidence of the cabin, whose site was later archaeologically tested and mapped by University of Tennessee students and Rugby volunteers under Dr. Charles Faulkner. The family descended from English and Scots-Irish immigrants who settled northern Morgan County around 1811; the Massengale line reached back to Yorkshire, England, and later to Virginia and North Carolina before Matthew Massengale and his sons moved from Ashe County, North Carolina, to Tennessee in the early 1800s. A Tennessee land grant in 1829 placed Dempsey Sr. near White Oak Creek, and records show that Dempsey Jr. and his Cherokee wife Betty Ann lived in adjoining Scott County and belonged to Longfield Baptist Church from 1850 to 1857 before they were living here by 1860 with six children; their youngest son, William Grant, was born here in 1867. Dempsey Jr. died in the mid-to-late 1880s and Betty Ann in 1892, and family accounts say William Grant later remained in the cabin with his wife Mary Atterson and their first four children before moving to nearby Robbins by 1905; the abandoned cabin stood into the early 20th century and was dismantled, probably in the 1920s, with its logs and stone reused elsewhere. Family life and the homesite were preserved through photographs, a watercolor and sketches made during visits in 1887 by Mrs. Taylor and her daughter Lucy, and through Lucy's journal entries about Betty Ann and her sister, as well as a 1901 photograph by Elmer Foote. Some of Uncle Dempsey Massengale's tall tales also survived through Esther Walton, including his story of killing a deer, a jack fish, and a wild turkey with one shot. An 1879 letter from John Boyle to Oliver Temple also records that the Massengales at first agreed to sell their property to the British colonizing group connected with Rugby, then abruptly withheld the signed document.