In 1860, Bowling Green was a thriving city of about 2500 inhabitants with many local businesses, a woolen factory, a candle factory, several mills, an iron foundry, and a newspaper. The city was vital to the war effort of both sides because of its transportation network, including the L&N (Lousiville-Nashville) Railroad, road network, the Big Barren River, and the hills that surrounded it. Beginning in mid-September 1861, a Confederate force of about 4500 men under General Simon Bolivar Buckner entered the city and constructed eight forts on available hilltops, with fortified positions also placed at key river fords and ferry crossings. Fort Webb defended parts of the Big Barren River, a ferry crossing, and a boat landing, and had three cannons mounted. Unlike more elaborate limestone-block fortifications such as Fort Lytle and Fort C.F. Smith in Bowling Green, Fort Webb was a simpler earthworks fort, or redoubt, built by soldiers using picks and shovels to dig a ditch and throw the dirt onto the parapet, forcing any attacker to charge the fort, descend into the ditch, and climb the steep scarp wall of the parapet to storm it. Its main visible structure is an earthworks lunette, a standard military engineering form shaped like a crescent moon and often built to protect artillery. Where erosion has exposed large pieces of limestone embedded in the earthwork wall, the stones served not as reinforcement but as a building guide, with rocks or logs outlining the lunette's size and shape before soldiers buried them with soil from the outer ditch.