Hugh Rogan returned to the Cumberland Valley in 1780 with John Donelson and other settlers who completed the harrowing river journey from Fort Patrick Henry (in upper East Tennessee near the Virginia state line) to Fort Nashborough (Nashville) where they joined with a group led by James Robertson who had come overland to the same place. These men, women, and children were the vanguard of permanent settlement. Hugh Rogan's name is among the list of about 250 men who signed the Cumberland Compact, a temporary instrument of government for the new settlements in the valley of the Cumberland River. Rogan spent nearly two decades helping to establish and defend several of the eight forts or stations called for in the Cumberland Compact.
From legal documents and from accounts by Rogan's contemporaries, including Donelson, William Hall, later governor and Congressman, John Carr, and Joseph Brown, we learn about Hugh's life and his adventures. For example, he was granted around 300 acres in Sumner County, established in 1786 as part of North Carolina. He also received around 300 acres for being among the first to plant corn after arriving in 1780. Rogan traded that parcel, in Davidson County near where Vanderbilt University is today, for another 300 acres in Sumner County, giving him a holding of 640 acres.
Rogan's property was along Bledsoe's Creek in an area called Greenfield. He shared a property line with Isaac Bledsoe and another neighbor was Nathaniel Parker, who married Mary Ramsey, the widow of Isaac’s brother, Anthony. Other settlers in this historic area, that includes Bledsoe's Lick in the Castalian Springs community, were Revolutionary War veterans William Hall, John Morgan, David Shelby, John Carr, and George and James Winchester and their families.