Founded by veterans of the Florida Indian Wars (1835 -1858), the first pioneers of Winter Haven arrived in the 1860's and farmed the fertile area with strawberries, eggplant, guavas, tomatoes, peaches and pepper. By 1900, the population had grown to 400 and Winter Haven contained citrus groves, a school, a post office, a real estate office, a Social Club, churches, stylish Winter Haven hotels, floral nurseries, a canning factory and the headquarters of the Florida Growers Association. Winter Haven was incorporated in 1911, and by this time had acquired banks, a band, a newspaper, a movie theater and 15 automobiles. The Florida Boom of the 1920s brought land speculation and in 1923 the Florida Citrus Festival was first held to salute this important local agribusiness.

In 1930, the first Publix supermarket opened in Winter Haven and in 1936 Dick Pope launched the world famous Cypress Gardens. State Farm Insurance has its regional headquarters here and Sherwin Williams, Wal-Mart, and Scotty's all have large distribution centers in the area. Other sectors the local economy include Winter Haven hotels, agriculture, cattle, light industry, health care, retirement and tourism. Top area attractions include Cypress Gardens, Bok Tower Gardens, the Fantasy of Flight Air Museum, Cleveland Indians spring training and the American Water Ski Hall of Fame.

The Winter Haven-Lakeland area of Polk County was ranked the 13th most affordable place to live in the United States by the National Home Builders Association and Money magazine ranked Polk County as one of the top 10 places to live in. The Winter Haven metropolitan area has approximately 75,000 residents with 30,000 people residing in Winter Haven's city limits.

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