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1920
During World War II, the Seaboard Air Line Railway, turned over part of the depot for use as a USO club. Bea Bridges headed the club and recruited the townswomen to take over the task of decorating the depot and entertaining the troops. Dan House contributed a jukebox, and every Saturday night the main base at the airport came into town to enjoy music and refreshments.
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1920’s
The roaring 20s did not pass Naples by. During these racy times, the towns people and winter visitors danced the Charleston under the stars to phonograph music on the pier. Signs were erected, which read: “do not throw fish on the dance floor.”
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1921
Ed Frank built the very first Swamp Buggy in 1921. The swamp buggy innovation was a necessity for people to travel during the rainy season. Ed Frank helped organize the first Swamp Buggy race in 1949.
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1925
The City’s first Mayor, Speed Menefee, served for less than one hour. On April 13, 1925, Mayor Menefee took the oath of office, then resigned during the meeting when it was learned that the commission of the Notary Public who performed the Mayor’s swearing-in ceremony had expired. Town Council quickly appointed E.G. Wilkinson as the new Mayor of Naples.
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1927
In January 1927, the Orange Blossom Special raced into town and transportation by train opened a new era in Naples history. The current Naples Depot was at one time a working train station. 1972 was the last train to depart from Naples.
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1928
The Naples baseball team of 1928 was considering the best in Southwest Florida. the team played in Philadelphia Athletics at their training camp in Fort Myers improved be a formidable opponent.
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1928
After the Tamiami Trail was completed in 1928, stations were built along the road in 10-mile intervals. Travelers could buy gasoline, food and drink, in their operators double does police. Once every hour, there are required to mount their motorcycles and patrol the trail. This colorful organization, the Southwest Mounted police, was disbanded during the depression.
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1936
Naples first softball team was organized in 1936. The Naples Tigers were Wilson Dyches, Felix Mills, Jack Mills, George Fox, Albert Cameron, Bill Tiptons, A.L Day, and H. House.
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1936
The first school in Naples, built in 1905, was a one room structure at 151 Broad Avenue South. All grades were taught by one teacher. The second school building was built in 1924, between 10th and 11th Avenues South on 4th Street South. In 1936, when a school was built on Third Avenue South, now Gulfview Middle School, the school buildings on Fourth Street South were divided into four residences.