Joseph and Green Chaires, cotton plantation owners, were granted a charter for the company.
The original plan was for the road to start near Newport, Florida and run to near Thomasville, Georgia with spurs to Tallahassee, Monticello and Quincy.
The Plank Road intersected Old St. Augustine Road and it was near that intersection that during the Civil War, Captain Patrick Houston's father, Edward Houston, built the small "Old Fort" with earthworks still to be seen in a small city park in the Woodland Hills subdivision.
Although the "Old Fort" or Fort Houston was built during the Civil War and is associated with the Battle of Natural Bridge, Captain Houston and his Kilcrease Light Artillery were nowhere near there during that battle.
Rather his artillery was positioned near the center of the Confederate line at the Battle of Natural Bridge.