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"

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

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.

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.

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

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.

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

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.

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).

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."

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.

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

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.

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.

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.

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

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.

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

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

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

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.

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.

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

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

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.

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.

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.

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.