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The Greatest Railroad Story Ever Told: The Florida East Coast Railway’s Key West Extension

By Seth H. Bramson

This article is a story of superlatives. Henry Morrison Flagler—Florida’s Empire Builder—was, is and always will be the single greatest name in the history of Florida, while the Key West Extension of the Flagler-owned Florida East Coast Railway was, is and will always remain—absolutely, positively, unequivocally, inarguably and incontestably—the greatest railroad engineering and construction feat in U. S. (and, possibly, world) history.

The building of that railroad was not just a matter or issue of “how,” but, more importantly, “when.” Almost everything the builders of the railroad did was a first, in engineering, in construction and in the art and discipline of American railroad building and operation.

There are those individuals (probably the same people who still believe the fable known in South Florida as “the orange blossom myth” who have been conned into believing that Mr. Flagler extended his railroad to the shores of Biscayne Bay because Julia Tuttle, one of Miami’s early pioneers, supposedly sent him some orange blossoms following the great Florida freezes of December of 1894 and January and February of 1895, an “event” that can be equated to a fairy tale, and which never occurred) who have had, through the years, the temerity to refer to the Key West Extension as “Flagler’s Folly,” a charge and comment that was and is pure, unadulterated hooey.

Although the first article propounding a railroad to Key West appeared in print (according to Sidney Walter Martin, on page 202 of “Florida’s Flagler”) as early as 1831 (Mr. Flagler then only a year old) with another article following in another Key West paper four years later, and although famed Confederate general John B. Gordon (one of the numerous high ranking former Confederate officers who, once the Civil War had ended, strongly supported full restoration of the Union) incorporated and chartered the Great Southern Railroad in Florida in 1870 with the right to build numerous lines within the state, including one to Key West, and even with the “National Geographic Magazine” article written by Key West’s famed collector of customs Jefferson B. Browne in 1896 propounding the building of a railroad through the Florida keys with Key West as its terminal, Key West, at the time that article was written Florida’s largest city, was not Flagler’s initial destination of choice.

The railroad’s terminal would, of course, eventually be Key West and it would be the railroad’s extension to the island city that would cement Flagler’s fame and legend for all time, but this is not simply a story of an incredible construction feat; rather, it tells of the life and times of the operation of a great railroad, how it was managed, who rode it, what it did for the Florida Keys and what it meant to the conchs, the residents of the keys and Key West.

In addition to the railroad, though, Flagler and the railroad’s (and the Florida East Coast Hotel Company’s) subsequent managers understood that there had to be ancillary services to make people recognize the usefulness, viability and need to patronize the railroad and its affiliates, hence there were the hotels, the Key West Terminal and the FEC Car Ferry Company, with its daily round-trips to Cuba, carrying vital railroad car loads of freight to and from Key West en-route to and from the rest of America. In addition, the Flagler System-owned Peninsular & Occidental Steamship Company provided regular passenger service from Knight’s Key to Havana (1908—1912) and from Key West to Havana thereafter and all of that is part of this incredible story.

The reader may be aware that there have been several books written on or about the Key West Extension, but except for the very first one, Pat Parks’ original 1968 “The Railroad That Died at Sea,” which, although giving a brief history of the line, focused on the construction and on the terrible Labor Day, 1935 hurricane, which ended service on the Keys segment of the railroad. The other books have either dealt almost exclusively with the construction and engineering challenges of building the railroad that went to sea (Dr. Dan Gallagher’s heavily researched “Florida’s Great Ocean Railway” the single finest example of that genre) or on the September second, 1935 storm, which swept away more than forty miles of roadbed and right of way, destroyed the Long Key Fishing Camp and killed more than 800 people. Those books, of which there have been several, also discussed, to relatively limited extents, the aftermath of the storm.

The book published in 2012 to celebrate the great feat’s Centennial, which has the same title as this article, is a first: it is the first book written on that great project that not only explains how and why the route to Key West was chosen and who the important figures were during the railroad’s construction, but it will also examine and discuss the daily operation of the railway and how it was maintained, the reason for opening the Long Key Fishing Camp (the Flagler System’s only casual inn or resort) and the later (1918-20) construction by the hotel company of the Casa Marina at Key West.

That book includes, for the first time in print, photos of many of the stations and the rights of way and, of course, the bridges, as well as views in, of and at the Trumbo Point, Key West terminal, in effect, bringing the operation of that great railroad to life.

The 1935 hurricane (with photos in the book never before published, including the only known views of the train which had been caught in the storm at Matecumbe after it had been brought back to Miami’s Buena Vista Yard) brought about the abandonment of the railroad south of Florida City (just south of Homestead) and the conversion of the right of way to the over-the-sea highway following that storm. The memory of that great project, and of those who have worked so hard and for so long to insure that what was done to connect the Keys to the mainland between 1904 and 1912 will never be forgotten, hence tribute is warmly paid, here and in the finale of the book, to, among others, Claudia Pennington, Director of the Key West Art & Historical Society and Board of Directors President David Hamilton Wright and their colleagues, for the magnificent exhibit at the Custom House in Key West which will forever memorialize the great task. Historians Joan and the late Wright Langley, Jeanne and Irving Eyster and the Matecumbe Historical Trust, which they founded, the late Dr. Dan Gallagher, whose research efforts and marvelously informative books have preserved and maintained so much in photographs and information, and Ed Swift and Steve Strunk, who did so much to preserve the memories of the Extension, as well as others who have played a role in preservation, must also never be forgotten.

And for those who were fortunate enough to enjoy their ride (or rides!) on the over-the-sea railway and were able, en-route, to tarry long enough to feast on a marvelous lunch at Long Key Fishing Camp and relish the freshly caught broiled pompano, the key lime pie and the iced coffee in the dining room at the main lodge, with a nonpareil view of the Atlantic, they might have gotten to meet the beloved American author, Zane Grey, the President of the Long Key Fishing Club, who perhaps stopped at their tables to visit and chat. In any event, please take your coach or parlor car seat or settle back in your Pullman sleeping car room and re-live with me the greatest railroad story ever told.

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