Maytown was the name given to a small settlement that developed at the junction of two railroad lines. The first line, completed in 1885 by the Atlantic Coast, St. Johns and Indian River Railroad Company, connected Titusville to Enterprise. Following the two freezes during the winter of 1894-95, which devastated the region's citrus crop, Henry Flagler was able to acquire this line for his Florida East Coast Railway at a low price.

In 1911, the FEC Railway began construction on a new cutoff, connecting to the Enterprise Branch at Maytown. It was completed to Okeechobee in 1915, a distance of 122 miles. This line lasted until 1947, when a new line from Okeechobee to Fort Pierce made it unnecessary. The Enterprise Branch was also abandoned, and as of 2008 its trackage had all been removed.

A few people remain in little Maytown. The old Enterprise Branch railbed, now owned by the Florida Department of Environmental Protection, is to become the longest rails-to-trails project in Florida.