Benjamin Estill was born on March 13, 1780 at Hansonville (now Russell County). He received an academic education and attended Washington Academy (now Washington and Lee University). He studied law and was admitted to the bar, settling in Abington to practice. He became Washington County's Commonwealth Attorney and a Delegate from 1814-1817.

Estill was a great advocate for the formation of Scott County. He was a great admirer of Winfield Scott, with whom he agreed in politics, and thus sought to honor him. The county seat of Scott was given the name Estillville (now Gate City). From 1825-1827, he was elected to the 19th Congress. Estill received almost every vote cast in the election. Beginning in 1831, he served as 15th Judician Circuit Judge for the counties of Lee, Scott, Russell, Washington, and Tazewell. Judge Estill served until his retirement in 1852.