The Florida Keys Overseas Heritage Trail exists thanks to Henry Flagler’s Florida East Coast Railway.
The Key West Extension, as the stretch from Homestead to Key West was known, was built between 1905 and 1912.
It was widely known as Flagler’s Folly by those that didn’t believe it was possible or worthwhile to traverse the remote Florida Keys archipelago with 42 bridges.
Flagler’s vision was to connect Florida’s largest city at the time, Key West, to the mainland, and then linking with freight lines to Cuba and the Panama Canal. He was also excited to bring tourists to the southernmost city — another link in his chain of luxury resorts along the east coast of Florida. The Key West Extension cost $30 million of Flagler’s personal fortune to build and he was 75 years old at the start.
On Jan. 22, 1912, Henry Flagler was onboard the first train to ride the length of the railroad from Homestead into Key West. He and his entourage were met by 10,000 ecstatic residents and dignitaries. The remarkable feat was now being labeled the Eighth Wonder of the World. He died a year later after a fall in his Palm Beach home.
While the railroad is long gone, the Florida Keys have been left a gift of 23 historic bridges, all at or approaching 100 years old. These are the centerpiece of the Overseas Heritage Trail, making it unlike any other trail in the country. All of these engineering marvels have been listed on the National Register of Historic Places.
There are three styles of bridges along the Overseas Heritage Trail. The spandrel arch was used over shallow water. This style can be seen at the Long Key Viaduct. Tall concrete piers with steel deck plates were used in depths of 20 feet or more. This style can be seen at the north end of the Seven Mile Bridge. The one-mile crossing between Bahia Honda Key and the Spanish Harbor Keys, had the deepest water (over 30 feet) and the strongest current along the route. While this difficult point was almost declared the “end of the line,” the engineers settled on using very tall cement piers topped off with trusses. By using trusses instead of deck plates they were able to reduce the number of pilings from 64 to 34.
The Overseas Railroad was shortlived. As local legend often tells it, the Key West Extension went out of commission after the Labor Day Hurricane of 1935 ripped through Islamorada. While this was certainly a deadly storm, Flagler’s railroad could have easily been repaired. However, it was a complicated time. Not only was the country still in the grip of the Great Depression, the railroad was in receivership. On top of this, the automobile was becoming the more preferred means of transportation. The state was already building a highway alongside the train tracks where possible, so the timing was opportune to sell the right of way to the Overseas Road and Toll Bridge District. The selling price 23 years later: $640,000.
Today the Department of Environmental Protection’s Office of Greenways and Trails is in partnership with the Department of Transportation and Monroe County to build a 106-mile multi-use trail from Key Largo to Key West. Built on the foundation of the Overseas Railroad, this new trail will be an alternative transportation route for locals and visitors alike who enjoy biking, hiking, paddling and fishing. The mission of the OGT is to not only maintain the historic bridges but also to interpret the era in which this amazing “folly” turned “wonder of the world” was built.
Visit the trail’s site here or call the Office of Greenways & Trails in Key Largo at 853-3571.
Monica Woll is a trail specialist with the Florida Keys Overseas Heritage Trail.