Although Spanish and English explorers had surveyed the St. Johns River during the early history of the peninsula, it was not until 1838 during the Second Seminole Indian War (War of Indian Removal) that the wilderness around Lake Monroe was opened to settlement by American colonists with the construction of Ft. Kingsbury and the widening of the St. Augustine Trail.
Ft. Kingsbury, named after Lt. Charles Kingsbury who died of fever at Ft. Mellon, was located on the north shore of Lake Monroe to the west of Green Springs, as illustrated on the MacKay and Blake army maps of 1838-39. The log stockade was a “satellite” fort of Ft. Mellon across the lake, and one of a line of posts from New Smyrna to Tampa intended to drive the Seminole Indians south. The St. Augustine Trail can be seen coming into the fort from the northwest and heading southeast through present day Osteen.
At that time, the interior of the Florida peninsula was traversed by a network of trails, including the St. Augustine or Old Spanish Trail. Starting from St. Augustine, this trail wound through thick hammock and pine forests down to Volusia, Spring Garden (now DeLeon Springs), Beresford, Lake Monroe, and points in south Florida. The St. Augustine Trail, probably based on ancient Indian paths, also linked to the Old King’s Highway along the coast. It was widened by the Tennessee Volunteers during the Second Seminole Indian War around 1837 when Ft. Kingsbury was constructed. The trail entered the area of present day Enterprise parallel to North Street roughly along the original route of Court Street to the lake. Parts of it can still be traced through Enterprise.