Anna Maria has the distinction of being the first Anna Maria Island city where settlers established homes. The first homesteader on the entire island was George Emerson Bean, a world traveler from Connecticut. He built his home near the present location of the Rod and Reel Pier in 1893 and homesteaded 140 acres, from the North Point (Bean Point) to what is now Magnolia Avenue, where the Island Community Center is located. His son, George W. Bean, became the first land developer and with John Roser formed the Anna Maria Beach Company. Streets and sidewalks were aid out; homes and a water system were built.
In 1911, before there was a bridge, a dock was constructed into Tampa Bay at the end of Pine Avenue. Excursion boats made daily trips, docking at the pier bringing supplies and visitors to the island.
In 1913, John Roser built the first church on Anna Maria Island on Pine Avenue. The lighted cross on the steeple of Roser Memorial Community Church was a beacon for fishermen. Captain Mitch Davis, the first mayor of Anna Maria City, was elected in 1925, just after the city was incorporated. Following the incorporation, electricity was brought to the island.
The first school was built on Magnolia Avenue in 1930, where the Island Community Center stands today. The Island Players Theater, at the Gulf end of Pine Avenue, was a home in the farming community of Parrish before it was floated down the Manatee River in two sections on barges.
Transportation on the island was by horse and wagon until Cortez Bridge was built in 1921. The rickety, wooden bridge was replaced by a modern concrete structure in 1957. Another bridge was built at the same time in Holmes Beach linking the island to Bradenton. The mail was brought from the mainland in the early 30’s by a colorful character, Harry “Uncle Sam” Ditmas, who once requested that the sheriff lock him in jail for the night because his wife was so angry at him.