Harry Stringfellow came to Pine Island in 1910 after the mail boat he arrived on ran aground near Pineland. A year later, he purchased a home on property near Alcorn Street in Bokeelia and planted a citrus grove. At the time of Stringfellow’s arrival, there were no roads on Pine Island – only paths and trails. The lack of roads prompted Stringfellow to run for Lee County Commissioner. After winning the election, he immediately began planning for roads on Pine Island. Since his going to Fort Myers for county meetings was a three-day event. His biggest challenge was a bridge over Matlacha Pass. Shell and fill were dredged from this area in order for a bridge to be built and in the process, the island of Matlacha was formed. The new bridge and road Stringfellow had built shortened his trip to Fort Myers to one day.
Soldiers stationed in Fort Myers during WWII soon discovered the great fishing off of the Matlacha Bridge and it soon became known as “The most fishingest bridge in the world.” The local fishing industry, shrimpers and bait shops, also grew giving Matlacha its fishing village character.
During the 1950’s and 1960’s canals were dug increasing residential waterfront. The original wooden bridge was replaced in 1969 with a concrete drawbridge, then again in 2012.
Today, Matlacha is a tourist destination with its many shops, restaurants and art galleries, which feature local artists and artists from all over the country.