Named indirectly for Simon Bolivar, South American statesman, general and patriot. It might have been called "New Prospect," but for a mug of rum. When town was founded in 1852, a man who had settled here from Bolivar, Tenn., wanted to name the community in honor of his hometown. But a preacher-doctor insisted that it be named New Prospect. An election was called to settle the matter and the Tennessean exchanged mugs of rum for votes, Bolivar won. During the 1800s, Bolivar was the westernmost fort in Denton County and the first settlement west of Collin County. Two stagecoach lines changed horses here. The town thrived and could count three hotels, several stores, a gin, a flour mill, a sawmill, a blacksmith shop, a saloon, a church and a school. It was here that the Texas cattle trail joined the Jesse Chisholm Trail, but it was John Chisum, Texas cattle baron, who had herds here and furnished beef to the Confederacy during the Civil War. Bolivar and the surrounding area were havens for Sam Bass and his men. Two Bolivar men were jailed in 1890 for harboring notorious marauders. Many early settlers (whose descendants still live here) played important roles in development of county.