Weakley was born in Halifax County in the Colony of Virginia on July 20, 1764, and he attended schools in Princeton, New Jersey.

[2] On April 18, 1782, Weakley left his home in Halifax County with a horse, bridle and saddle, and $1.75.

He went to Rowan County, North Carolina to study surveying with General Griffith Rutherford.

During the winter of 1783, he moved to the Cumberland settlements, and set up residence on Whites Creek in Davidson County.

He and Thomas Bedford, a fellow land speculator, were granted as assignees a North Carolina land grant and had laid out 102 town lots and a Public Square by 1803, at the junction of the East and West Forks of the Stones River.

[4] In 1785, Weakley moved to the part of North Carolina that later became Tennessee and engaged in agricultural pursuits.