This deed is the legal origination of land that eventually served as my father’s family childhood homeplace.
James Douglass was an appointed deputy surveyor of Colonel William Preston, county surveyor, when Kentucky was known as Fincastle County of Virginia. In April 1774, Douglass joined John Floyd, Hancock Taylor (uncle to future US President Zachary Taylor), and Isaac Hite in heading to Kentucky. Other members of the surveyors group soon joined.
Although surveys had been conducted in the region a year or so prior, those claims were not considered legitimate because the men conducting the surveys were not deputized by Col. Preston.
In the detailed account, The Fincastle Surveyors in the Bluegrass, 1774 by Neal O. Hammon, around July 3, 1774, Douglass, having left the headwaters of the Elkhorn, “discovered a spring which he named Jessamine after his daughter, an only child.” This spring of Jessamine Creek served as the primary water supply for the my father’s homeplace.
He has shared memories of how integral was that spring to his youth. Finding arrowheads, swimming, how it would swell and on a few occasions shot up like a geyser, how he saved his older brother from drowning there, when the bridge was built…and more. I knew the creek spring as where the family gathered for my uncle’s pig roasts.

Attempts to transcribe the handwriting and legal jargon of this time the late 1700s were a bit futile. When I am able to get clarity, I can revisit and update the references. I am building the timeline for how Douglass’ deed eventually came to be owned by Pleasant Cook, my 2nd great grandfather.
Words I can decipher – James Douglass, 1,000 acres, the District of Kentucky, 5 or 6 miles below Hickman creek, head of Jessamine Creek, a remarkable camping place.





















