In 1539, Hernando de Soto's expedition passed through La Florida with a similar route.

Spanish colonial officials began constructing a stone fort, which was unfinished in the mid-1760s when Great Britain took over.

Twenty years later when the Spanish returned, they kept the East and West divisions, with the administrative capitals remaining at St. Augustine and Pensacola, respectively.

A former British officer named William Augustus Bowles attempted to unify and lead 400 Creek Indians against the Spanish outpost of San Marcos, capturing it.

Two captive British citizens, Robert Ambrister and Alexander Arbuthnot, were tried, found guilty of inciting Indian raids, and executed under Jackson's authority – causing a diplomatic nightmare between the U.S. and Britain.

The U.S. Army garrison of 200 infantry and artillery men occupied the fort for the better part of a year (1818–1819).

In 1821, Florida was ceded to the United States and Fort St. Marks, as the Americans called it, was again garrisoned by U.S. troops.

It is the fountain-head of a river... and is of sufficient volume to float a steamboat, if such an affair had yet dared to penetrate this solemn wilderness...

The water is so astonishlingly clear that even a pin can be seen on the bottom in the deepest places, and of course every animate and inanimate object which it contains is fully exposed to view.

The apparent color of the water from the shore is greenish, but as you look perpendicularly into it, it is colorless as air, and the sensation of floating upon it is that of being suspended in a balloon; and the water is so refractive, that when the sun shines brilliantly every object you see is enveloped in the most fascinating prismatic hues.Another possible origin for the name Wakulla, not as widely accepted, is that it means "mist" or "misting", perhaps in reference to the Wakulla Volcano, a 19th-century phenomenon in which a column of smoke could be seen emerging from the swamp for miles.

The town of Port Leon was once a thriving cotton-shipping hub, with a railroad from Tallahassee that carried over 50,000 tons of cotton a year to be put on ships, usually for shipment direct to Europe.

[3][4] During the Civil War, Wakulla County was blockaded from 1861 to 1865 by a Union Navy squadron at the mouth of the St. Marks River.

The Battle of Natural Bridge eventually stopped the Union force that intended to take Fort Ward and nearby Tallahassee, the only Confederate state capital other than Austin Texas which had not been captured.

The Union was not able to land all of its forces, but they still outnumbered the Confederates, who chose to make their stand at a place where the St. Marks River goes underground: the "Natural Bridge" referred to.

[4] Today, Wakulla has several doctors and dentists, several supermarkets and big-box retailers, a golf resort, and a thriving seafood business.

[8] Wakulla County was added to the Tallahassee, Florida Metropolitan Statistical Area (MSA) in 1973.

The Georgia, Florida and Alabama Railroad, completed in 1893, passed through Sopchoppy on its route between Tallahassee and Carrabelle until its abandonment in 1948.

Sixteen miles (26 km) of that right-of-way became the Tallahassee-St. Marks Historic Railroad State Trail in 1988.