DRIVING THE KEYS – Upper Keys History - A vintage photo of a man driving a car - Florida Keys

Politician George Allen began advocating for a road to the Keys in 1895. In 1908, residents of Monroe County (and especially Upper Keys farmers) began clamoring for a better road system on the islands. 

With the arrival of Henry Flagler’s train, life in the Keys began transitioning away from being a boat culture. Farmers needed better roads to move their crops from their fields to the packing houses becoming established near the railroad. 

In 1922, Monroe County officials allocated $300,000 for road projects, including a road from North Key Largo’s exclusive Anglers Club to the Key Largo train depot, once located near Mile Marker 105.5. 

Also built was a road that paralleled the railway south to Upper Matecumbe Key and projects on the Lower Keys and Key West. 

In 1926, Monroe County issued a $2.5 million bond for further road projects. That would create State Road 4A, also known as the first incarnation of the Overseas Highway. 

J. Otto Kirchheiner, chairman of the Monroe County Commission, is credited as the first person to traverse the highway via automobile, leaving Key West for the mainland, July 18, 1927. State Road 4A officially opened to public traffic on Jan. 25, 1928.

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