Webster

Webster claims the title of Sumter County's oldest community, settled around the mid-1850s by pioneers drawn to the fertile farm country of central Florida. It grew up as an agricultural town, and its identity has always been tied to the land — vegetables, citrus, and cattle. Webster was once known as the "Cucumber Capital of Florida" for its vegetable production in the early twentieth century, and the early-season Parson Brown orange — named for a local pastor — is commonly traced to the area. The city was formally incorporated in 1925.

Webster's enduring claim to fame is the Sumter County Farmers Market, established in 1937 and billed as Florida's oldest and largest continuously operating flea market. The market's famous Monday-only rhythm is itself a piece of Depression-era history: "blue laws" kept business off Sundays, so local farmers shifted their trading day to Monday, and it stuck. Today the market sprawls across roughly 40 acres of sheds, pavilions, and open lots, drawing produce sellers, antique dealers, and tens of thousands of bargain-hunters during the season.

For all that fame one day a week, Webster itself stays tiny — recent estimates put the city's population under 1,000. It sits in southern Sumter County amid streams, small lakes, and working farms, and in recent years has gained the Florida Grande Motor Coach Resort, an upscale RV-resort destination a few miles from downtown. Proximity to the booming Villages area to the north has begun to pull more attention toward this quiet corner of farm country.