Fort Cass, a U. S. military installation was established here in 1838, and from this facility General Winfield Scott directed all aspects of the Cherokee Removal, now commonly called the “Trail of Tears.” The actual contract for removing the Indians was given to John Ross, the man who had been elected Chief of the Cherokees for a four year term in 1828. Although his elected term of office expired in 1832, he continued to use the title “chief.” Ross hired Captain Henry B. Henegar as wagon master and clerk for the project. Captain Henegar accompanied the Indians all the way to Oklahoma, and remained with Ross until he was settled in that location. For a year he lived as a part of the Ross household, acting as the Agent for Ross in the disposal of government equipment. He then returned to Tennessee and served with Major Samuel Milligan in Mexico as contractor for war supplies during the Mexican War. After the war, he came back to Charleston and built an imposing brick Federal style mansion on the spot where the Fort Cass barracks had formerly been located. “As time went on,” his daughter later wrote, “Father engaged in farming on an extensive scale. A comfortable house was on what we called the creek farm, and there ‘Uncle Bob’ and his wife ‘Aunt Hiley’ lived with several more of the colored people.”  (2)

The Henegar House in Charleston, Tennessee
in the late 1800’s

A combination of geographic and outside factors caused Charleston to take on an importance far greater than would be expected from its size and population. From the earliest times, the Hiwassee River has been an important artery of transportation. For thousands of years the Indians had used large dug-out canoes on the river. The Anglo-Americans brought flatboats and keelboats. Almost every farm and plantation along the river had its boat landing. Colonel Meigs used flatboats to transport the produce of local Cherokee Indians down river to Chattanooga from the agency. An important aspect of the Hiwassee River is that its tributary, the Ocoee River flows only eleven miles from the Conasauga River, a stream that provides a water route to the Gulf of Mexico. It was possible to pole a keelboat up the Hiwassee and Ocoee to Peter Hildebrand’s boat yard where wagons carried the goods the short distance to David McNair’s boatyard on the Conasauga. This route, eliminating the time and cost of using the Mississippi River to get to the Gulf, became very popular. In early 1821, a keelboat fifty feet in length, called The Tennessee Patriot, made the trip with a hundred barrels of flour and whiskey. At one time a canal was proposed to connect the Ocoee with the Conasauga, but the project was never completed. The coming of steamboats increased commercial traffic on the Hiwassee River and much business was conducted at the Charleston Dock. A local man stated: “Every time Charleston gets something Cleveland takes it, but they won’t be able to get our steamboat.”  (3)

Some early steamboats

The railroad brought an even greater significance to Charleston. Plans for a railroad line linking Chattanooga and Knoxville were being talked about as early as 1837, and in 1842 a bridge was constructed over the Hiwassee River at Charleston. It did not, however, become a railroad bridge until 1851.  On June 10, 1851 Miss Myra Inman wrote in her diary: “Cars came to Cleveland today for the first time.” On September 15, 1851 there was a major celebration throughout the county. The occasion was the fact that the East Tennessee and Georgia Railroad had reached the Hiwassee River. Trains ran back and forth all day long between Charleston and Cleveland, each carrying all the passengers they could accommodate. By 1858 all of east Tennessee was connected with lines extending south into Georgia and to Chattanooga.  (4)

Having a railroad connection brought more steamboats up the Hiwassee to Charleston. Some of these were the Loudon, the Union, the Tennessee, the Kingston, and the Holston. General James Gamble, a veteran of the War of 1812, purchased the Union, and obtained a contract for transporting the copper ore from the mines in Polk County.  He brought the ore down the Ocoee and Hiwassee to Charleston, where it was transferred to railroad cars on the way to the refinery.  (5)
Charleston and the Hiwassee Valley was a vibrant and rapidly growing place on the eve of the American Civil War when the National census of 1860 was conducted. The county had been in existence for less than thirty years, and there was a feeling of newness everywhere. Like most southern communities of that day, the county was a series of sprawling farming communities with little difference between one and the other. Besides Charleston, the only other real town was Cleveland, the county seat. Even there, many of the residents called themselves farmers and there was no clear distinction between the rural fields and urban streets since many residents maintained a town lot, as well as a farm. The Henegar family in Charleston maintained a farm south of town as well as the large house on Market Street.  (6)