Socks With Crocs
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How Winter Garden Became Winter Garden

Posted October 20, 2026 · 10 pages

Want More Winter Garden History?

We barely scratched the surface.

If you want to see the photographs, artifacts and stories behind Winter Garden’s railroad, citrus and community history for yourself, stop by the Winter Garden Heritage Museum in downtown Winter Garden.

Appropriately enough, the museum is housed in the city’s historic railroad depot — one of the surviving pieces of the railroad story that helped build Winter Garden in the first place.

The museum is operated by the Winter Garden Heritage Foundation, which has spent decades collecting, preserving and sharing the history of Winter Garden and West Orange County.

Admission is free, and donations help support the Foundation’s preservation work.

Winter Garden Heritage Museum
1 N. Main Street
Winter Garden, FL 34787

Learn more and plan your visit →

And if you’re already on Plant Street, you really have no excuse.

It’s basically sitting right there.

The Short Version

Cliff Notes

  • It started with agriculture. Settlers began farming around the southern shore of Lake Apopka in the 1850s, taking advantage of the area's fertile soil and warm climate.
  • Nobody is completely sure how Winter Garden got its name. Stories range from winter-grown tomatoes sprouting from discarded seeds to local growers simply describing their ability to garden through winter.
  • The railroad created the town we recognize today. Rail service connected local farms to distant markets and helped establish Plant Street as Winter Garden's commercial center.
  • Citrus became king. Groves and packinghouses dominated the local economy for generations, turning Winter Garden into an important agricultural center.
  • Lake Apopka was once a tourist attraction. Before theme parks defined Central Florida tourism, visitors traveled to Winter Garden to fish for Lake Apopka's famous largemouth bass.
  • East Winter Garden has its own important history. The city's African-American community developed around Center Street, with residents playing major roles in citrus, agriculture, local businesses and civic life.
  • Winter Garden nearly lost the industries that built it. Lake Apopka's environmental collapse devastated fishing, while freezes in the 1980s helped push much of Central Florida's citrus production farther south.
  • Downtown declined — and then came back. Preservation efforts beginning in the 1990s protected historic buildings, while the former railroad corridor became part of the West Orange Trail and helped bring people downtown again.
  • Modern “Winter Garden” is much bigger than the actual city. Huge portions of Horizon West use Winter Garden mailing addresses despite being outside municipal limits.
  • And then there's “Disney West.” Keep going south toward Flamingo Crossings and the Winter Garden address starts feeling considerably more Disney than old Florida railroad town.