Historic Downtown Homestead The City of Homestead is the second oldest city in Miami-Dade county. The South Dade area opened to homesteaders in 1898. At the time the only way in and out of the area was through a path called the "Homesteaders Trail". In 1904 Henry Flagler decided to extend the railroad to Key West from Miami. Farmers of the local area were now able to transport their fruits and vegetables to Miami and other parts of the state. Many of the workers who helped build the railroad stayed in the area and became the founding founders of our city. In 1912 the Overseas Railroad was completed and in 1913 the City of Homestead was incorporated.