Section 2.1: Escapists, Entrepreneurs & Early Industry

Where Flagler’s railroad once blazed a path, today the Overseas Highway leads travelers through the heart of the Florida Keys.

South Florida’s history has something of an escapist theme to it. First, the Seminole tribes trying to escape forced extraction from their ancestral lands by the U.S. government—and refusing to concede—fled to the inhospitable swamps of Big Cypress, eventually becoming today’s successful entrepreneurs of casinos, resorts and heritage museums.

In the Florida Keys, settlers escaping hard lives and former slaves escaping from the South trickled in from the north, turning Key West into a thriving port town of Cuban cigar making, sponge harvesting, salt production and fruit orchards. 

Enter railroad magnate Henry Flagler, whose Florida East Coast Railway chugged down Florida’s entire eastern seaboard, bringing with it assorted dreamers, opportunists and those simply seeking a better life. 

It was a floodgate that never closed, and visitors can follow the timeline of the famous and infamous who streamed into South Florida and the Keys during the late 19th and early 20th centuries by visiting local museums as well as the homes they left behind.