The center of activity in the Enterprise area moved a mile west along the lake in the early 1850s when Jacob Brock, the most prominent steamboat captain on the river, saw the potential of the site as the head of navigation on the river. Florida had become a mecca for invalids seeking a healthier clime and a new wave of well-off travelers seeking adventure in the newly promoted Florida wilderness. Brock had transported many of them on his Jacksonville line.
In 1851 Brock started purchasing land in the present area of Enterprise, laying out streets and lots, and building a wharf. The property he bought included a wood frame store and possibly a small boardinghouse. Virgil DuPont, probably related to the large and influential DuPont family in St. Augustine, had already acquired a land grant near a small flowing spring later known as Benson Springs near the present Progress Energy Power Plant and ran a small hotel with a post office and surrounding orange grove.
By 1854, Brock would complete his own 100-room hotel that would put Enterprise on the map as “the premier destination on the St. Johns.” From his wharf he operated the first regular line of steamboats from Jacksonville to Lake Monroe.