Farmers built a small wooden train station here soon after the Orange Belt Railroad reached the area in 1886, and by 1899 the Taveres & Gulf Railroad had added a second rail line and nearby depot. Wooden stores rose alongside the parallel tracks, and Winter Garden was incorporated in 1908. From 1910 to 1960, prosperity drove the town's growth as it became a major citrus shipping point and downtown served as the region's shopping center, while nearby Lake Apopka gained fame as "the large-mouth bass capital of the world." In the second half of the 20th century, the city center declined as automobiles replaced train travel, strip malls surpassed downtown Plant Street stores, and Lake Apopka became severely polluted. After multiple freezes during the 1980s decimated the citrus industry, many buildings in the deteriorated downtown district stood mostly abandoned. Orange County replaced the Plant Street railroad tracks with the West Orange Trail in 1994, helping spark a turnaround, and in 1996 a district with 24 commercial structures was listed on the National Register of Historic Places. Strong efforts by residents, merchants, and city officials then helped bring about the city center's rebirth.