In the early 1920's Harry Stringfellow, a resident of Pineland and Chairman of the Board of Lee County Commissioners, gained approval for the development of a road to Pine Island. The shell fill that was dredged from the oyster beds of Matlacha Pass was used to build the entire road and create the Land mass that is now Matlacha. A wooden swing bridge was set in place over the pass and in 1927 Commissioner Stringfellow led dignitaries across the completed route.

Soldiers stationed in Ft. Myers during World War I discovered the great fishing off the bridge and it soon became known as the "Fishingest Bridge in the World". Driven by the depression, squatters began building shacks on the excess fill. A fishing industry, cannery, shrimpers, and bait shops grew giving Matlacha its quaint fishing village character.

During the 1950's and 60's canals were dug, thereby increasing residential waterfront availability. The old wooden swing span was replaced with the present concrete draw bridge in 1969.