Bolivar, founded in 1852 and named indirectly for Simon Bolivar, was nearly called New Prospect until a settler from Bolivar, Tenn., traded mugs of rum for votes in an election and secured the name for his hometown. During the 1800s, it was the westernmost fort in Denton County and the first settlement west of Collin County. Two stagecoach lines changed horses there, and the town prospered with three hotels, several stores, a gin, a flour mill, a sawmill, a blacksmith shop, a saloon, a church, and a school. It was the place where the Texas cattle trail joined the Jesse Chisholm Trail, and John Chisum had herds there and furnished beef to the Confederacy during the Civil War. Bolivar and the surrounding area also served as havens for Sam Bass and his men, and two local men were jailed in 1890 for harboring notorious marauders. Many early settlers, whose descendants still live there, played important roles in the county's development.