The area now known as Winter Garden was once home to a large number of Native Americans. Artifacts found around the lake indicate that Indians inhabited the land for thousands of years, up until the colonization of Florida by Spanish explorers. The earliest European settlers, attracted to the fertile muck soil around Lake Apopka, began arriving around 1845 after the Armed Occupation Act encouraged settlement and Florida became a state. Trade goods were transported south on the St. John’s River to Mellonville (Sanford), across sandy trails by horse, mule and oxcart to The Lodge (later known as Apopka), then floated across Lake Apopka to the south shore.

It wasn’t until the Orange Belt Railway arrived in 1886 that the community really began to grow. With this rail line and the later addition of a second railroad, settlers began arriving in the area to take advantage of the fertile soil, mild temperatures, and good transportation. When farmers built a train depot in 1893, they named the stop “Winter Garden” in honor of the year-round growing opportunities here.  Citrus became the “cash crop” in the area and farmers planted large tracts of orange groves. The city grew quickly as more and more boxcars of vegetables and fruit were shipped out of the two downtown train stations.

In the 1920s, with the arrival of paved highways and the Model T, Florida became a tourist destination. Winter Garden attracted fishermen who heard stories of the “large-mouth bass capital” known as Lake Apopka. Local businessmen pooled their resources and built the Edgewater Hotel in 1927, a state-of-the-art inn built to accommodate fishermen. Trailer City, located on the lake, was one of Central Florida’s earliest trailer camps, built in the1930s with funds from Roosevelt’s New Deal. In addition, twenty-five fishing camps lined the shores of the lake, offering many amenities to attract tin-can tourists.

During the 1940s, Winter Garden proclaimed itself as the largest citrus shipping point in the world. Eight citrus packing houses were located within the city limits. Hoyle Pounds opened Pounds Motor Company in downtown Winter Garden in 1920 and for more than 80 years, citrus farmers from across the state came to purchase and service their farm equipment there. At one time, Pounds operated the nation’s largest Case tractor dealership east of the Mississippi. In addition to selling equipment, Hoyle was famous for adapting farm equipment for better use in the citrus industry. His most famous invention was rubber tires for tractors.

During World War II, the citrus industry boomed as the federal government, eager to provide soldiers with vitamins necessary to fight disease, purchased large quantities of canned orange juice to send to troops around the world. The Winter Garden Citrus Growers Cooperative built a juice plant to take advantage of the demand. After the war, sales of the metallic-tasting canned juice diminished somewhat. Luckily, shortly after the war, scientists invented better tasting frozen-concentrated orange juice and the demand for the product sky-rocketed. The Winter Garden Citrus Growers Association began manufacturing frozen concentrate in April of 1950. As the industry soared, the city prospered.

Beginning in the 1960s, things took a downward turn. It began with the pollution of Lake Apopka. Water quality damage became apparent from years of effluents dumped by sewage treatment and citrus processing plants, as well as fertilizers and pesticides from vegetable farming around the lake. High-nutrient effluents in the lake encouraged wide-spread algae blooms, blocking sunlight, choking productive submerged plants and causing a decline in game fish populations. By 1970 Lake Apopka was no longer a fishing destination.

In addition, new shopping centers and malls lured shoppers away from downtown stores and the construction of interstate highways caused a decline in the use of railroads for travel and fruit shipment. Winter Garden’s downtown shopping district and two train stations stood idle. Still, despite the 1971 opening of Walt Disney World, West Orange County continued as a citrus economy. That was to soon change.

In 1983, Central Florida experienced the first of three devastating freezes within six years, killing orange trees throughout the area.  With each freeze, more and more farmers succumbed to pressure to sell their valuable land to developers, moving their groves further south, where temperatures were a few degrees warmer. The citrus economy of Winter Garden plummeted.

Thankfully, the abandoned railroad line that runs through the heart of historic downtown became Orange County’s West Orange Trail in 1994. Today, approximately 40-50,000 visitors use the trail every month. Trail users are delighted by the 2003 streetscape renovation, the early twentieth-century brick buildings and the nostalgic feel of our “charming little city with a juicy past.” New restaurants, shops, the Heritage Museum, the Central Florida Railroad Museum and the Garden Theatre occupy the once-empty historic buildings of the National Historic Register Business District.  Winter Garden is a thriving community once again.