The Enterprise midden or shell mound accumulated over thousands of years from the debris of cooking and toolmaking by the ancestors of the Mayaca.

[4] Beginning in the First Spanish Period, Florida Indians fell victim to European diseases, forced labor, missionization, and slave raids from the English militia of the Carolinas allied with invading tribes from the north.

By the 1760s, Florida's native cultures including the Mayaca, Timucua, Apalachee, Ais, Surruque, Calusa, and Tequesta had been decimated.

Taylor built an inn atop the shell midden to attract visitors traveling by shallow-draft steamboat from Palatka, the furthest upstream that ocean-going vessels could navigate.

Orange groves were planted, and a gristmill established, together with a sawmill to cut Southern live oak, prized by the U.S. Navy for warships.

In 1851, Jacob Brock bought land a mile west of the original settlement, where he built a wharf and laid out streets and lots.

A steamboat captain with "a notable reputation for the lavish and original nature of his profanity", he had transported to Enterprise many invalids seeking the climate and sulfur springs, which were believed to be curative for a variety of ailments.

It was a 206-mile (332 km) trip aboard the Darlington, which departed Jacksonville at 8:00 AM on Saturday, timed to receive passengers discharged from ocean-going ships.

The South Atlantic Blockading Squadron division commanded by Union Captain George Balch set out to capture Confederate steamboats on the St. Johns River.

Seized at Lake Monroe on March 14, 1864, was the Hattie Brock, named for the captain's daughter, and loaded with 150 bales of cotton for export to help finance the rebel cause.

[citation needed] Following the rebellion, the state experienced a boom in tourism, and Enterprise became a fashionable resort and sportsmen's paradise for fish and game.

Never popular, the name "Benson Springs" changed back to "Enterprise" in 1937, the year the deteriorating hotel was razed to increase room for the 'Florida United Methodist Children's Home.

EPS was helpful in obtaining protections from Volusia County, including designation as a Community of Special Interest, implementation of the Enterprise Local Area Plan, which establishes additional landscape and architectural standards, and finally the designation of the Enterprise Historic District, encompassing several blocks of the historic downtown area.

Following Several years of renovation and thousands of hours of volunteer work, it reopened as the Enterprise Heritage Center & Museum in October, 2014.