The Historical Society museum displays artifacts, photographs, and maps that show the Island's history from its earliest times as an Indian fishing camp, to the Island's roaring twenties culture, to the first homesteader in 1893, to the baseball players who once wintered here in the 1950s-70s. The historical building features the original City Jail, the Belle Haven cottage that once sat on the City Pier, and a garden of plants from Anna Maria Island's history.
Each exhibit in the museum has its own history ranging from the first settlers and their legacy to the history of the island's fishing and baseball. A person can also dig into their own history or another person's with the ability to see records and newspapers.
Out back of the Anna Maria Island Historical Society, the old jail can be found. The jail now offers a place where visitors take pictures with family and friends. However, when the jail was built in 1927 it originally handled late night disturbances for a new bar on the West end of Pine Avenue. Anna Maria City needed a spot to hold the tavern goers when they had disturbances and needed time to cool off. The jail had a wooden roof with bars that left jail goers open to mosquito swarms and plenty of bites all night. The jail caught on fire during a wind storm in the 1940s and ever sine the jail had been used as a popular Anna Maria city photo opportunity.
Carolyne Norwood, the founder of The Historical Society, was the author or the book named The early Days. This book is offered by The Historical Society to provide more fascinating facts about the Anna Maria Journey from 1893-1940.