Harry Stringfellow came to Pine Island in September of 1910 from Mexico City. He became a Lee County Commissioner in 1926. His commute from Pine Island to Fort Myers for commission meetings was a three-day ordeal that began at his home near Pineland, travel over trails by horse to St. James City, where he boarded a steamboat to Fort Myers. It took a day to get to Fort Myers, another day for meetings and a third day for the return trip home. Stringfellow served on he commission from 1926 to 1953. He was instrumental in having the county install the Matlacha Bridge linking Pine Island with the mainland. He also played a role in having the main north/sourth road put in on Pine Island, and that road bears his name today.