In the decade following the Second Seminole War (1835-1842), tension between settlers and Seminole Indians prompted Federal authorities to establish a trading post in Florida's interior. The Kennedy-Darling Trading Post was built on the northern end of the Seminole reservation, easy for the Seminoles to reach, but away from settlements. The trading post, constructed in the spring of 1849, was attacked and destroyed in July of that year by defector Seminoles. Reports of the attack motivated the U.S. Army to establish a chain of fortifications across the Florida peninsula. This line of forts across the northern boundary of the Seminole reservation was intended to protect the settlers to the north and provide bases for the Army to control the Seminoles. Work began on Fort Chokonikla, the first in the chain, on October 26, 1849. The fort was built on high ground near the former trading post. The Seminoles did not want war and the fort never came under attack. Casualties, however, were high and the Army was nearly defeated by disease-carrying mosquitoes.

In July 1850, due to sickness among troops, Fort Chokonikla was abandoned and never reoccupied. In 1978, the Fort Chokonikla site was placed on the National Register of Historic Places. The state acquired the land containing the Monument, Trading Post and Fort Chokonikla in 1974. The park, now 410 acres, opened to the public in 1981. Although nothing remains of the fort or the trading post, visitors can learn about the history of these at the park's Visitor Center.