The Florida Keys Over-Sea Railroad


A Historical Timeline of the Rise and Fall of the Florida Keys Over-Sea Railroad

Highlights compiled by the Key West Art & Historical Society and Seth H. Bramson, a company historian of the Florida East Coast Railway and author of the recently released “The Greatest Railroad Story Ever Told: Henry Flagler and the Florida East Coast Railway’s Key West Extension”

1830 –  Henry Morrison Flagler is born in Hopewell, N.Y., on Jan. 2.

1831 – In a report to the U.S. Senate, a Key West newspaper argues a strategic advantage of building a railroad to Key West and that the island town can serve as a great naval base.

1870 – Standard Oil is incorporated in Ohio and becomes the largest oil refiner in the world.  Notable Standard Oil principals include John D. Rockefeller, Flagler and Samuel Andrews.

1878 – On advice of his physician, and due to his wife’s illness, Flagler travels to Florida for the winter and stays in Jacksonville.

1885 – Henry Flagler makes his first purchase of a railroad, buying the Jacksonville, St. Augustine and Halifax River Railway, a narrow-gauge line that ensures delivery of supplies to three hotels Flagler is building in St. Augustine. That railroad is later renamed the Jacksonville, St. Augustine and Indian River Railway.

1889 – The Florida legislature sets aside 10 million acres of land to be deeded to entrepreneurs willing to build new railway lines.

1891 – Henry Flagler has a conversation with Jefferson Browne, then president of the Florida state senate, regarding the merits of building a rail line to Key West, especially if the Panama Canal becomes a reality.

1895 – Following in the footsteps of the previous winter, another hard freeze hits Florida. The hard freezes ruin citrus crops and vegetable farms as far south as Palm Beach, leading the way for William and Mary Brickell and Julia Tuttle to convince Flagler regarding the potential of developing Miami. The Brickells offer Flagler half of their holdings on the south side of the Miami River. Tuttle offers Flagler half of her land north of the river plus 50 acres of her land for a railroad terminal, shops and yards. In September, the name of the Jacksonville, St. Augustine and Indian River Railway is changed again, this time to Florida East Coast Railway (FEC).

1896 – Flagler’s FEC Railway line from Jacksonville to Miami is completed on April 15. Jefferson Browne, Collector of Customs for the Port of Key West, lays out an almost complete route for the railroad to follow to Key West in an article for “National Geographic.”

1897 – The FEC Hotel Company acquires a hotel known as the Hotel Key West. The hotel eventually becomes known as the Jefferson Hotel and the FEC Hotel Company does not have a presence in Key West until plans for the Casa Marina Hotel begin in 1914.

1901 – Flagler, 71, marries Mary Lily Kenan, a 34-year-old North Carolina debutante.

1903-04 – William J. Krome surveys the Everglades to see if a cross-state railroad is possible. His two surveys show that it would not be and Flagler directs him to survey a route to Key West.

1904 – Flagler decides to build the Over-Sea Railroad, but no official announcement is made.  During that time, surveyors and engineers work to provide Flagler with data and information. In May, the United States formally acquires the Panama Canal Zone. In July, the rail line to Homestead is completed.

1905 – Early in the year, preliminary surveys and mappings of channels and water over the Keys are completed. The FEC Railway begins construction of the extension from the mainland to Key West and completes the first rail section connecting Homestead to Jewfish Creek. State Bill 11 becomes law granting the FEC Railway rights to build the Key West Extension and granting the company a 200-foot right-of-way down the Keys.

1906 – The FEC Construction Division begins building a landfill for a railroad terminal in Key West that eventually covered 134 acres of land.

1907 – Central Supply in Islamorada is fully operational. Roadbed is finished on Stock Island.

1908 – A bridge to span the seven-mile stretch of water below Marathon is planned. On Jan. 22, the first regularly scheduled train from Miami to Knight’s Key (Marathon) arrives and the Over-Sea Railroad is a half-finished dream.

1910 – Workers drive the first spike at the Key West end of the Florida East Coast Railway on the Trumbo Island railhead.

1912 – A special Pullman sleeping car train leaves New York City Jan. 20, headed for Key West. On Jan. 21, FEC engineers place the final steel plate girder (span 36 of the Knight’s Key bridge) permanently in place. FEC engine 201 arrives in Key West at 2:45 a.m., the first engine and crew to cross the Bahia Honda Bridge and test tracks in the Lower Keys. The first FEC train arrives in Key West at 10:30 a.m. Jan. 22 with Flagler, now 82, and his wife Mary Lily Kenan in his luxurious office car with three bedrooms, a kitchen, salon and private bath. Following a Jan.  23 parade to commemorate the opening of the Over-Sea Railroad, a banquet is staged in the marine barracks where a message from President Taft is read and Flagler makes a brief speech.

Regular passenger service begins Jan. 22 with a 5 p.m. departure from Key West to the mainland.

At 11 a.m., Jan.  26, the first excursion train leaves Key West for Long Key to help familiarize Key Westers with a new way to travel at moderate prices. Some 123 passengers make the trip, which, after a short stay, returns around 6:30 p.m. The roundtrip fare is $2.60.

In 1922, the coach fare from Jacksonville to Key West is $20.34 and roundtrip exactly double. Bramson estimates the fare from New York City to Key West — using several different rail lines was approximately $77.

1913 – Henry Flagler dies May 20 at the age of 83 at Whitehall, his home in Palm Beach.

1914 – Plans for the Casa Marina Hotel in Key West begin, but ground is not broken for four more years. Panama Canal opens.

1921 – The Casa Marina Hotel formally opens Jan. 1 for its first season that runs through April.

1926 – The economic boom in south Florida and the Keys goes bust. Monroe County citizens overwhelmingly approve a $2.5 million bond issue to launch construction of an “Overseas Highway.”

1927 – A severe winter, followed by a cool summer in northern Europe, causes charges that dredging and filling for the Over-Sea Railroad bed had caused a change in the path of the Gulf Stream. Europeans charge Flagler with displacing their climate control, but the U.S. Hydrographic Bureau and the Weather Bureau find no reason to believe the Key West Extension has shifted the Gulf Stream in any way.

1928 – A road opens from Miami through Card Sound Road. Travelers can continue to Key West via a time-consuming and often unreliable ferry-and-road system.

1929 – Wall Street stock exchange crashes in October, beginning the Great Depression.

1931 – Having defaulted on its mortgage bond interest payments, the FEC becomes a ward of the Federal Bankruptcy Court in Jacksonville.

1933 – The Florida Legislature creates the Overseas Road and Toll Bridge District to complete a highway from Lower Matecumbe Key to Big Pine Key to eliminate ferries.

1935 – The September Labor Day hurricane devastates the Upper and Middle Keys, killing many and rendering Key West inaccessible by a direct land route for the first time since 1912. Miles of embankment are washed away and in some places the railroad track is washed a great distance from the roadbed. The bridges, however, survive with minor damage. The U.S. is in the grip of the Great Depression and the FEC, still in receivership, is not in position to put money into repairs.

1936 – Both the Key West City Council and the Key West Chamber of Commerce pass similar resolutions calling for the abandonment of the Key West Extension and “to proceed without delay” to supply the Florida Keys and Key West with satisfactory and adequate transportation via an overseas highway. In September, the U.S. Interstate Commerce Commission approves the application from the FEC to abandon the Key West Extension and in October bids for construction of several sections of the Overseas Highway are opened with high hopes for a completed highway before the close of the 1937-‘38 winter season. The U.S. Public Works Administration offers to lend the Overseas Road and Toll Bridge District $3.6 million to acquire 45 miles of right-of-way and other properties of the FEC between Lower Matecumbe and Big Pine Key stations to convert the route into an automobile highway.

1938 – On July 2, the Florida Keys Overseas Highway officially opens to Key West using the FEC abandoned right-of-way and standing bridges as the route for a highway through the Keys.


A Conversation With Celebrated Historian, Seth Bramson

Bramson displays a signal lantern from the original Over-Sea Railroad. Images courtesy of Seth Bramson

Standard Oil millionaire Henry Flagler conceived the Florida Keys Over-Sea Railroad soon after the dawn of the 20th century, and the first train traveled from the Florida mainland to Key West Jan. 22, 1912. Today historians credit the railroad, officially named the Key West Extension of the Florida East Coast Railway, with making possible the evolution of the modern Florida Keys.

Seth Bramson is a company historian for the Florida East Coast Railway and author of “The Greatest Railroad Story Ever Told: Henry Flagler and the Florida East Coast Railway’s Key West Extension,” the recently released history of the engineering and construction of the railroad that stretched more than 100 miles over open water. Nationally recognized as Florida’s leading transportation historian, Bramson says he has amassed the world’s largest collection of FEC Railway and Florida transportation memorabilia.

A celebration commemorating the 100th anniversary of the Over-Sea Railroad’s completion culminates Jan. 14-23 in the Florida Keys, with its final event a Jan. 23 evening presentation and book signing by Bramson at The Studios of Key West, 600 White St.

Here, the historian shares insights into the railroad that connected the Florida Keys with each other and mainland Florida for the first time.

Q: How complex was the construction of the Florida Keys Over-Sea Railroad? What other large-scale construction projects does it compare to?

Seth Bramson: The building of the Key West Extension was the greatest single railroad engineering and construction feat in U.S. — and possibly world — history. During the era of the extension’s construction, the only engineering feat that could be even remotely compared to the Key West Extension’s construction was the building of the Panama Canal.

Dignitaries who attended the train's arrival were each given gifts, a replica of one of the supports from the Over-Sea Railroad.

Q: What were the most daunting engineering challenges in the construction process?

SB: Unquestionably, the most daunting engineering challenges were the building of the three major bridges: Long Key Viaduct, Bahia Honda Bridge and what is today known as (the) Seven Mile Bridge, as well as the filling of open water to create the Key West Terminal property, today known as Trumbo Island. Nothing like the building of the bridges had ever before been attempted. In order to successfully complete them, concrete which hardened under water had to be brought from Germany, as no American concrete at that time was able to harden under the great ocean pressures at the depths at which the bridge piers had to be placed.

Q: What did construction of the Over-Sea Railroad mean for Flagler and his team?

SB: The successful completion of the Key West Extension added to Flagler’s legacy to the point that today the name Henry M. Flagler is the single greatest name in the history of Florida.

Q: What were the Florida Keys like before the railroad was built?

SB: Prior to the completion of the Key West Extension of the FEC, the Keys were completely rural and mostly uninhabited. The FEC brought life to the islands as well as hospitality venues. Whole communities came into being because of the railroad, including those at Marathon, Matecumbe, Long Key and others.

Q: How did the Over-Sea Railroad change the Florida Keys?

Although the year is unknown, this promotional post advertises the one-day trips to Miami from Key West that were organized by the Miami Chamber of Commerce.

SB: The completion of the railroad to Key West meant the fulfillment, to the people of the Keys and the island city, of one word: accessibility. With the coming of the railroad, the isolation ended and, although it would take time and patience, development could and did begin. The Keys were, with the completion of the railroad, a completely different world.

Q: The railroad operated for less than 25 years, but it left an indelible legacy. How does its existence continue to affect the Keys?

SB: The building and operation of the Key West Extension of the Florida East Coast Railway was, and is, the greatest railroad story ever told. The incredible task of building a railroad over the sea in the early years of the 20th century has come in no small measure to define the residents of the Keys — the Conchs — who have come to be known for their hardiness, their pluckiness, their adaptability and their resilience.

Q: Why should people care about the centennial of the Over-Sea Railroad’s completion?

SB: It is extremely important that, especially given the issues and problems that America faces today, the celebration of what America was — and still is — capable of doing should and must be celebrated and memorialized.


History of the Florida Keys Over-Sea Railroad

(Content contributed by  Jerry Wilkinson, Florida Keys historian)

To build the Florida Keys Over-Sea Railroad, originally known as the Key West Extension, Florida East Coast Railway owner Henry Morrison Flagler needed an unusual team.

For its leader he chose Joseph Carroll Meredith as his chief construction engineer. The 28-year-old William Krome became the assistant construction engineer. As this would be an overseas project, Flagler purchased, leased, or built most of the heavy marine equipment in the east. Land had to be donated, purchased, or leased, as Flagler did not receive land grants in the Keys other than water passages – he did own land preciously granted to other railroad companies that he had bought. So many of the transport ships in the Atlantic were employed solely to transport supplies and materials for Flagler that it created a minor shortage for transporting other goods. It was a massive operation.

Using Krome’s survey, plans were made to send advance teams ahead to start the more time consuming projects and the overland clearing throughout the Keys. Functional seaports and rail terminals had to be built at Knight’s Key and Key West. The large bridges could not be started until huge floating concrete mixers could be constructed. Concrete mixer number 1 was towed out of Miami on June 27, 1906. Work was begun throughout the Keys, not just one huge work force moving southwest from Homestead. Over 130 acres of land was to be dredged/pumped in for the Key West Terminal. The work camps were, however, numbered from north to south from Homestead. Key Largo was camp 1 and Key West was camp 82.

By the spring of 1905, construction teams were dispersed throughout the Keys. From the mainland, in April, two of the ten traveling dredges set out from what would become Florida City across Cross Key to Jewfish Creek. One dredge worked on each side of the right-of-way, piling up fill to form a track rail bed in the center. Rock was transported and spread. Tracks were laid on top of this rock foundation. The Woodall and Everglade stations were built on side tracks located where the vehicle passing lanes of the 18-mile stretch are now, now (2007) being removed for a new 3-land highway.

This was time consuming work, but not difficult. Jewfish Creek presented them with their first bridging challenge. It had to be a drawbridge to permit boat traffic even in those days also being replaced by a 65-foot fixed span bridge.

The overall goal was Key West; but the intermediate goal was Knight’s Key Dock. The immediate task was to lay as much track from Homestead as possible. This allowed Flagler to use his railroad mounted equipment, or “rolling stock,” which could carry huge loads, make more trips and deliver directly to the place of need. The water was too shallow for larger transport ships, so they used 150 huge barges to ferry supplies to shore.

An October 28, 1905 Miami Metropolis newspaper clipping provides some indication of work: “The steamer Biscayne towed and delivered to the Keys two of the remaining double-decked houseboats [living quarters] recently completed. One of the boats will locate at Planter and the other at Matecumbe Key where camps will be established, both being under the charge of Engineer Rogers.”

W. P. Dusenbury was the engineer in charge of work on Key Largo. The Jewfish Creek bridge was not finished when the track arrived; however, difficulty in building a stable causeway across Lake Surprise was a greater concern. The lake was to be filled, not bridged. When fill was dumped in, it sank and disappeared. It appears that it took 15 months to construct a satisfactory fill that would support continuous trains across Lake Surprise.

Labor was a constant problem. The pay was $1.25 a day with food, lodging and medical care. Along with labor, lack of fresh water and mosquitoes constantly haunted the project. It is said that a total of 40,000 men, but never over 5,000 at any one time, were employed. An average of 4.5 million gallons of fresh water was required each month.

From an unidentified clipping dated June 27, 1906: “Concrete Mixer No. 1 was hauled out from the north end of the (Miami) terminal dock, and towed to its destination in the Keys by the steamer Columbia. This is an indication that the arch and bridgework is soon to begin. Mixer No. 2 is about ready [for delivery].”

An October 29, 1906 Florida Times-Union newspaper clipping indicated progress: “Some weeks ago engine No. 10, intended for use in construction work on the Keys, arrived from St. Augustine. This morning the same engine and several box and flat cars were sent down the line to Homestead, then south 17 miles on newly constructed track to the coast of Jewfish Creek. At that place they were loaded onto barges and ferried across the stream [Jewfish Creek and Lake Surprise] to Key Largo. Engineer Goethe had the honor to pull the first train of cars on the Florida Keys.” A day later, another report related that there were 27 miles of track on which to operate on Key Largo.

Work was proceeding more or less on schedule, yet with a few exceptions like Lake Surprise and an October 17, 1906 hurricane that dealt a staggering setback with 130 men known to have perished, during the work on the Long Key bridge. The Flagler team learned to respect the hurricane season and not be caught off guard again.

From an article in February 10, 1907: “The first train crossed from the mainland to Key Largo (last Friday) with Henry Flagler and a party of friends aboard.” It appears that the Jewfish Bridge and the Lake Surprise causeway were finally operable.

And in a March 12, 1907 article, two years into the project: “The greatest center of activity is centered at Long Key and the lower end of Upper Matecumbe Key, though there is building and construction at other points with trains now running to Tavernier and Snake Creek.”

Rail Service to the Upper and Middle Keys

The first train to reach Knight’s Key Dock (Marathon) by rail did so on January 20, 1908 at 1:30 p.m. Saturday afternoon. By February 4, 1908, a twice-a-day daily schedule was in effect. The following day travelers boarded a Flagler Peninsular & Occidental steamship bound for Havana. A seaport city had been built south of Knight’s Key, complete with a railroad station capable of handling two complete trains, docks for two small steam ships, hotel boat, customs and post office (April 13, 1907). Therefore, the Upper Keys had daily scheduled train service in early 1908.


Read more about the Florida East Coast Railroad and the Middle Keys