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The History of Leesburg Florida

Leesburg is Lake County’s oldest city and at one time was the county seat while a part of Sumter County. The city claimed 1857 as its birthday when Leesburg celebrated its centennial in 1957, recognizing the year that the city’s namesake, Evander Lee, and his family came to the area.


Evander McIver Lee was the first known settler, but others soon followed and many of them planted citrus groves.  Leesburg and surrounding Lake County became among the leading citrus producers in the world. 

While Lee became the area’s first permanent settler, Thomas Robertson and his 21-year-old son, John Marmaduke Robertson came to what would become Leesburg in 1843, or likely a year sooner. They lived in what would become the heart of Leesburg for 11 years before Thomas sold out and moved back to Moss Bluff. John later sold his property and founded the nearby community of Whitney. 

Evander Lee moved to the area in 1857, a year after his father died. They had moved to Adamsville from Alabama in 1849. Evander Lee brought with him his wife Susan and eight children. He purchased the old Thomas Robertson homestead from James Fussell for $3,300. Several Lee brothers also joined Evander, and his brother, Calvin Lee, is credited with giving Leesburg its name. Calvin and Evander had built a log store on Main Street where the public restroom is now located. When Calvin went on a buying trip to New York City and was asked where to ship the merchandise, he reportedly told his suppliers to bill his goods to "Leesburg." 


From Wikipedia:

Leesburg is a city in Lake CountyFlorida, United States. The population was 20,117 at the 2010 census. As of 2019, the population recorded by the U.S. Census Bureau was 23,671.[5]

Leesburg is in central Florida, between Lake Harris and Lake Griffin, at the head of the Oklawaha River system. It is part of the Orlando–Kissimmee–Sanford Metropolitan Statistical Area.

Leesburg is the home of Lake–Sumter State College (LSSC), which also has campuses in Clermont and Sumterville, Florida. It is also the home of Beacon College.

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Leesburg History Museum

In the early 20th century, Leesburg was an important center for watermelon production. In 1930, it held its first Watermelon Festival, an annual tradition that lasted for nearly 30 years. But gradually watermelon production dwindled and, for the last festival in 1957, watermelons had to be brought to the city from outside the area.

In 1938, during the Great Depression, the Franklin D. Roosevelt administration invested in infrastructure and improvement projects across the county. Its Works Progress Administration began work on the Venetian Gardens waterside park, located on the shores of Lake Harris. These canals and gardens have been a centerpiece of the community ever since.

Lake Square Mall, the city's major shopping mall, opened in 1980. On March 19, 1982, Ozzy Osbourne's guitarist Randy Rhoads, as well as the band's cook and bus driver, were killed in a plane crash at Flying Baron Estates.[6]

The citrus industry was the principal business in this area for decades, but devastating freezes in December 1983 and February 1985 persuaded growers to move their groves further south.


In 1997, Leesburg Bikefest started. It has since become an annual spring tradition, with upwards of 250,000 people attending every year.

Today, most of Leesburg's growth and economic development is the result of its increasing popularity as a retirement destination. In addition, the rapid growth of nearby Orlando has resulted in demand for housing here, as many people commute to Orlando for work. In 2011 and 2017, the Leesburg High School boys' basketball team won the 4A state championship.

The downtown area along Main Street has been redeveloped and now includes many fine shops and restaurants.  This area of Leesburg has a nice laid back small town atmosphere.

Belle of Florida Oranges Label
Leesburg Fire Dept in Christmas Parade
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From 1922 to 1924, the city's Cooke Field was used by the Philadelphia Phillies for their spring training sessions. On March 14, 1923, the stadium was used for the site of an exhibition game between the Phillies and the St. Louis Cardinals.


In 1936, the city built the Ballpark at Venetian Gardens, which was used by several minor league baseball clubs that played in the Florida State League from 1937 to 1968. The city won league titles in 1941 and 1946.


Since 2007, the city has been the home of the Leesburg Lightning, a wood-bat collegiate summer baseball team in the Florida Collegiate Summer League.


Shooting exhibitions

During the 1920s, sharpshooter Annie Oakley, who had a residence in Leesburg, performed shooting exhibitions at Cooke Field, including one for the Philadelphia Phillies.

Leesburg Lightning Logo-White.jpg
Pat Thomas Basebal Stadium.jpg
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