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Sunday Favorites: Anna Maria's first Settlers


Anna Maria Island wasn't settled until the 1880s. It stood as a rugged and sparsely inhabited barrier island with untamed wilderness, dense mangroves, and untouched beaches. At that time no bridges connected the island to the mainland. Those who visited had only one option, to access the island by boat.

George Emerson Bean is often credited as one of the earliest settlers of Anna Maria Island. Born in  Ohio in 1848, Bean arrived on the island in the  1890s. As a successful businessman and entrepreneur, Bean recognized the potential of Anna Maria Island for agriculture and real estate development. He purchased large tracts of land and played a significant role in its early development, including establishing a homestead, cultivating crops, and promoting tourism to the area, according to a 2018  historical talk presented by Alexa Schofield, of the Florida Maritime Museum entitled “Anna Maria’s Early Settlers and the Cortez Bridges.”

In 1897, Samuel and Annie Cobb made their move to Anna Maria Island, drawn to the location by tales from their predecessor George Emerson Bean. They settled at the island's northern end, eager to start anew. Just a short time after arriving at their newfound home, Annie birthed a daughter and named her Anna Maria, after the idllyic island paradise. 

However, as aspirations grew for Anna Maria's burgeoning settlement, it became evident that a bridge was imperative to accommodate the influx of visitors. A search commenced for the right candidate to undertake this pivotal task. After careful consideration, the spotlight fell upon Jack Leffingwell, the son of a prominent Bradenton physician. With his credentials deemed fit for the job, Jack was entrusted with the crucial mission of constructing the bridge, heralding a new chapter in the island's accessibility and growth.

Leffingwell, had no experience building bridges per se, but he was a man of diverse talents and pursuits. Jack's contributions to the community were significant and varied. He was an innovator, navigating the waters of the Manatee River on his bicycle-like pedal boat. But it was in the realm of communication infrastructure that Jack truly made his mark. Well, respected for bringing telephone and telegraph lines to Manatee County, he played a pivotal role in modernizing the community with the new technology.

Leffingwell’s first attempt to build the bridge did not turn out as well as his telephone endeavor. In 1921, he began the construction. However, the ambitious project faced a devastating setback when a hurricane swept through the area in October of the that year. The powerful storm wreaked havoc, obliterating the bridge entirely along with approximately 80 percent of the Cortez waterfront and its docks. Despite the widespread destruction, a handful of residential homes and structures managed to withstand the fury of the hurricane, including the 1912 Schoolhouse, which now serves as the Florida Maritime Museum. The school served as a refuge for those seeking shelter from the tempestuous winds and rains.

After the hurricane's passage, construction efforts on the bridge resumed. It wasn't until eight months later that the bridge was finally completed. The total cost of the project amounted to approximately $58,000 at the time. This bridge, erected in 1922, served as a vital link, connecting to Bridge Street in what is now modern Bradenton Beach. Remarkably, remnants of the original structure can still be found today at the historic fishing pier situated at the end of Bridge Street, according to Schofield. 

Wind and weather deteriorated the wooden bridge in a matter of decades, rendering it increasingly rickety. My mother, who spent her childhood in Palmetto, painted a vivid picture of the bridge's instability. She recalls moments during school field trips when crossing the bridge aboard a bus was downright frightful! Its narrow width and tendency to sway in windy conditions only heightened the sense of unease.

In 1957, the wooden bridge was replaced with a new one. To assure spectators of the improved durability, local politicians decided to parade an elephant across it to showcase its sturdiness. Governor Spessard Holland was among the public figures that attended the event.

Interestingly enough, the second Cortez bridge had a tollbooth, charging 30 cents for passage, but miraculously, the return trip fwas free! When the cost of the bridge was paid off in 1964, the toll booth was removed, sparking celebrations among locals as reported by the Islander newspaper.

The first bridge established Bridge Street as an instrumental hub of local business. However, the construction of a new bridge further north prompted efforts to preserve the now historic street. Utilizing remnants of the 1922 bridge as a fishing pier, an initiative aimed at showcasing the island's heritage and instilling a sense of pride  reimagined Bridge Street. The endeavor sought to ensure that the historical significance of the original bridge site remained prominent, emphasizing the rich legacy embedded within the community's collective memory.


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  • Carolannfelts

    As always, thank you for your wonderfully written and well researched articles on our area’s history!

    Carol Ann Felts

    Sunday, April 7 Report this