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History & Culture

OAKLAND
Today, Oakland remains a quaint, unhurried rural community much like it was in 1887, when the town was incorporated. The oak tree-lined clay streets are nostalgic reminders of an era when life was peaceful and everyone knew all their neighbors. The town folks still meet and greet their neighbors every morning when they pick up their mail at the Oakland Post Office. A 700-student charter elementary school is Oakland’s most recent achievement, affording area residents with a choice in their child’s education.

OCOEE
When Florida was a comparatively young state, people traveled from the north to the area now known as Ocoee. After the Civil War, confederate soldiers and their families founded the city of Ocoee. Captain Bluford Sims and General William Temple Withers were the first to settle in the area. It was Captain Sims who gave Ocoee its Indian name, which means “not cold.” For General Withers, Ocoee was his home only during the winter months for health reasons, therefore making him Ocoee’s first “snowbird.”

Together, Sims and Withers were responsible for the formation and construction of the Ocoee Christian Church in 1898. The Withers-Maguire House was also built in that year and today is listed with the National Register of Historic Places. Captain Sims also planted the first commercial orange grove in the county and laid ground for the future growth of Ocoee.

The city of Ocoee was incorporated in 1925 and has been a center for the citrus industry since the city’s founding in the last quarter of the 19th century. The citrus trees were originally brought into the area over Lake Apopka by barge and flat bottom boats, and led to the growth of the area with residents and businesses alike. With the coming of the railroad and the success of the citrus industry, more and more families moved to Ocoee. The hard work and dreams of the founders of Ocoee laid the foundation for all that we know today.

WINDERMERE
World traveler and Englishman Dr. Stanley Scott decided to make this picturesque spot his home in 1881. He named this land surrounded by sparkling lakes, Windermere, thought to be named after the district in England. Soon after, other settlers came to the area, many from England. In 1887, engineers of the Plant System of Railroads, who were constructing the Florida Midland Railway, laid out the first town site. In 1895, disaster struck the fruit industry and a dormant state of affairs loomed over the community until about 1910. It was around this time that J.C. Palmer and Dr. Howard Johnson discovered the town of Windermere. These two men played a dominant part in the growth and progress of the community. The beauty of the area impressed Mr. Palmer and he decided to build his permanent home in the deep woods of Windermere. For two years, Mr. Palmer resided in a roofless log cabin until he built his permanent house that is still occupied by members of his family.

Windermere was mainly a resort area in the early 1900s. Many visitors built winter cabins to enjoy the local fishing. The 1920 census recorded the population of Windermere at 182. In 1925, the town was incorporated, thereby restricting its boundaries, and the census decreased to 153. Windermere also played a part in history during World War I. The ladies of the town would meet regularly during the war to make surgical dressings. This resulted in the formation of the “Windermere Women’s Club.” In 1927, their clubhouse was moved to its present location in the center of town and is now the town hall. Today, Windermere is a quaint architectural mixture ranging from cabins to estate homes with sand roads to preserve the town’s chain of lakes and its history.

WINTER GARDEN
A gentleman named Mr. A.B. Newton moved to the area from Mississippi with a history of poor health. It was here that his health improved and he lived a long and healthy life. Mr. Newton credited the city for his miraculous recovery, so he bestowed the city with the name, Winter Garden.

Records trace land titles of property in Winter Garden back to about 1880. Transportation during these early years was by steamboat on Lake Apopka, but the steamship line went out of business when the first railroad was built in 1886. The railroad, or Orange Belt as it was called then, traveled from Sanford to St. Petersburg, Florida. The Orange Belt was later named the Atlantic Coast Line until it merged with the Seaboard Airline Coast Line. From this merger the Seaboard Coast Line Railroad was formed and provided freight service for the vast citrus industry from Winter Garden. Today, the Railroad Museum stands as a tribute to the vital form of transportation, which enabled the citrus industry in the area to flourish.

Incorporated in 1903 on the southern shores of Lake Apopka, Winter Garden was largely an agricultural community. Citrus and vegetables were the foundation of the area’s economy. Change came in the 70’s and the 80’s when several back-to-back winter freezes, combined with the opening of Walt Disney World, changed the nature of the area’s economy. Winter Garden adapted to the changing times and replaced the railroad tracks in the center of town developing the West Orange Trail, bringing people from all over the area back to downtown. Today, the Winter Garden Heritage Foundation operates three museums, including the Heritage Museum, the History Center and the Central Florida Railroad Museum, located in the heart of downtown. All offer educational field trips, community events, photographs and memorabilia. Many individual histories are preserved in the extensive collection of over 5,000 family files from those that have helped make the area what it is today.

In addition, the historic Garden Theater’s restoration, just completed, will become the heartbeat of the city as a performing arts center and movie theater. The economic and creative impact opens new and exciting possibilities for the entire West Orange County community.