Key West Extension (Overseas Railroad): History, Construction, Decline

Last revised: October 8, 2026

The Key West Extension, also called the Overseas Railroad, was the Florida East Coast Railway’s line from the mainland across the Florida Keys to Key West. Henry M. Flagler built it between 1905 and 1912 so that his railroad would end at a deep-water port, a coaling stop for ships bound for the Panama Canal, then still being dug, and a short sea crossing to Havana. From Miami the route measured 156 miles. From Homestead to the Key West terminal the company’s own 1912 booklet measured 128.4 miles, and 17.2 miles of that distance stood on bridges.

The last steel girder of the Seven Mile Bridge went into place on January 21, 1912. The next day Flagler, 82 years old, arrived in Key West in his private cars. The Labor Day Hurricane of September 2, 1935 broke the line. In 1936 the right-of-way was sold for the road that became U.S. 1.

Florida East Coast train, apparently a 4-8-2, ready to leave Trumbo Island in Key West on a late afternoon in 1933

A Florida East Coast train, apparently a 4-8-2, ready to leave the railroad’s terminal at Trumbo Island in Key West on a late afternoon in 1933.

On this page: At a glance · Why Key West · Building across the keys · The bridges · Three hurricanes · Knight’s Key · January 1912 · Trains and the Havana ferry · September 2, 1935 · The Overseas Highway

At a glance

Item	Detail
Railroad	Florida East Coast Railway. Also called the Overseas Railroad, the Florida Overseas Railroad, and the Oversea Extension
Route	Miami and Homestead to Key West, by way of Key Largo, Long Key, Knight’s Key, Bahia Honda, and the lower keys
Length	156 miles, Miami–Key West. 128.4 miles, Homestead to the Key West terminal, in the company’s 1912 booklet
Bridge work	17.2 miles: 11.1 miles of concrete-arch viaduct and 6.1 miles of steel on concrete piers
Longest bridge	Seven Mile Bridge, Knight’s Key to Little Duck Key, 35,815 feet
Engineers	Joseph C. Meredith, chief construction engineer, died April 20, 1909. William J. Krome finished the work. Clarence S. Coe was resident engineer on the Seven Mile Bridge
Work began	April 1905, after surveys. Ground broken in Key West on November 2, 1905
Interim terminal	Knight’s Key dock. First train from Miami, January 22, 1908
Opened	Last girder and a test engine, January 21, 1912. Flagler’s train, January 22, 1912
Last day	September 2, 1935, the Labor Day Hurricane
Sold	1936. Right-of-way from Florida City to Key West, $640,000, plus cancellation of $300,000 in taxes
Highway	A driver could reach Key West with the ferries gone on March 29, 1938. The new Seven Mile Bridge opened May 23, 1982

Why Key West

A railroad to Key West had been talked about for decades before Flagler had a mile of track in Florida. The Key West Gazette mentioned the idea in 1831. In 1870 the Great Southern Railroad was incorporated to run from Georgia to the island. General John B. Gordon took a franchise for a similar line in 1883 and abandoned the work before it reached the Florida coast. The island already mattered. In 1890 Key West, with 18,080 people, was the largest city in the state, a wrecking and cigar port closer to Havana than to the new towns Flagler was planting on the Atlantic shore.

Flagler talked with Jefferson B. Browne, then president of the Florida senate, in 1891. On April 29, 1893 the legislature chartered his Jacksonville, St. Augustine & Indian River Railway to extend “on and across the Florida Keys to Key West.” Browne’s essay “Across the Gulf by Rail to Key West” appeared in National Geographic in June 1896, the same spring the railroad reached Miami. The Spanish-American War, two summers later, made the naval argument in public. The Panama Canal, begun in earnest by the United States in 1904, supplied the commercial one: a ship leaving the canal for the Atlantic would want coal, and Key West sat on that track.

The first line the engineers favored left Homestead and crossed the Everglades to Cape Sable, then jumped about 25 miles of open water to Big Pine Key. William J. Krome’s surveys set that route aside. The railroad would go south to Key Largo and follow the islands. Jewfish Creek, the crossing onto Key Largo, was the chosen door. Joseph R. Parrott, the railroad’s president, put the question to Flagler and received the answer the construction force remembered: “Very well, go ahead.” Flagler hired Joseph C. Meredith as chief construction engineer in July 1904. The public announcement, and the start of work, came in April 1905. Flagler said he expected trains on January 1, 1908.

Building across the keys

Meredith had division engineers P. L. Wilson, Clarence S. Coe, G. R. Smiley, and Ernest Cotton, with R. W. Carter as bridge engineer. The force, at the busiest seasons, was more than 4,000 men. They lived in camps on the keys and on houseboats moored alongside the work. A central supply depot was operating at Islamorada by May 1907. Camp No. 10, opened in the summer of 1905 near the west end of Vaca Key, grew into the terminal later called Marathon. In March 1909 the construction headquarters moved from Miami to Pigeon Key, a speck of land in the middle of the water the Seven Mile Bridge would cross.

Shallow openings were filled. Dredges and traveling excavators built the embankments, and marl pumped onto the slopes hardened in the sun into a crust that stood up to waves. The 1912 booklet estimated another 20 miles or more of that embankment beyond the bridges. Meredith, short of coal and fresh water for ordinary dredges, had a gasoline dredge built. Where the water was too deep to fill, the railroad set concrete. European portland cement went into the underwater work. Cofferdams and caissons carried the piers down to rock. Fresh water, food, and cement all had to come by boat until the railhead arrived. Krome’s summary of those years was short: “We have put things through because we had to.”

An official 1930 system map of the Florida East Coast Railway, with the Key West Extension highlighted. Author’s collection.

The bridges

Four crossings dominated the plans. The company’s 1912 booklet put the whole of the permanent bridge work at 17.2 miles: 11.1 miles of concrete-arch viaduct and 6.1 miles of steel bridging on concrete piers. The longest, from Knight’s Key to Little Duck Key, was a little over seven miles with its approaches. Bahia Honda had the deepest water, some pier foundations 30 feet below tide. At Key West the booklet described a fill of 134 acres on the shallow north side of the island, made with hydraulic dredges, and a concrete pier 1,700 feet long and 134 feet wide reaching deep water in Man-of-War Harbor. The waterfront already stood full. The terminal had to be new land. Howard Trumbo, of the Trumbo American Dredging Company, built that fill. The first spike at the Trumbo Island railhead was driven on May 12, 1910. Flagler looked over the 134 acres on April 23, 1911.

Structure	Crossing	Length	What was built
Long Key Viaduct	Long Key to Grassy Key	2.68 miles	Concrete arches, 180 of them in the Quarterly’s count. The arch most often compared with a Roman aqueduct
Seven Mile Bridge	Knight’s Key to Little Duck Key	35,815 feet	Knight’s Key, Pigeon Key, Moser Channel, and Pacet Channel. 335 steel girder spans, about 9,000 feet of concrete arch, a 253-foot swing span at Moser Channel, 546 concrete piers. Steel set by Terry & Tench of New York. Work from the spring of 1909 to January 1912
Bahia Honda Bridge	Bahia Honda Channel	5,055 feet	Steel through trusses: thirteen spans of 128 feet, thirteen of 186 feet, one of 247 feet, and nine deck-girder spans. Deepest water on the extension
Boca Chica Viaduct	Boca Chica	A little more than half a mile	Concrete arches, the last long viaduct before Stock Island and Key West
Key West terminal	Trumbo Point	134 acres of fill	Hydraulic fill and a pier 1,700 by 134 feet. The railroad’s Key West station

The Seven Mile Bridge was four bridges in series, and the name came later. At the time it was the Knight’s Key, Pigeon Key, Moser Channel, and Pacet Channel crossing, sometimes called the Flagler Viaduct. The steel deck stood about 30 feet above low water. A swing span at Moser Channel let boats pass between the Atlantic and Florida Bay. Bahia Honda, shorter and harder, used pin-connected trusses because the builders wanted fewer piers in the deep channel. When the state later put automobiles on that bridge, the roadway was set on top of the trusses. That upper deck is still there. Between these great spans the railroad crossed a chain of shorter concrete viaducts: the channels of Key Largo, Toms Harbor, Spanish Harbor, the Pine and Torch channels, Niles and Kemp and Bow channels, and the Saddlebunch and Shark Key openings. A period account limited trains on the viaducts to 15 miles an hour. From a coach seat, on the long bridges, the water stood on both sides of the car.

Three hurricanes

The Quarterly called the hurricanes of 1906, 1909, and 1910 the greatest obstacle on the work. The October 1906 storm hit the Long Key camp the hardest. Houseboat No. 4, with about 150 men aboard, broke its moorings and was carried through Hawk Channel into the Gulf. Published counts of the dead run from 130, the Quarterly’s figure, to 164 killed and 81 injured on the Key West Art & Historical Society timeline. Equipment and finished grade went with them. Meredith’s sentence after that storm was the rule the job kept: “No man has any business connected with this work who can’t stand grief.” The crews went back to work through hurricane season. One manager said it was cheaper to sink the floating plant in protected water and raise it after the blow.

On October 10 and 11, 1909, another hurricane crossed the keys, did damage counted in the millions, and set the promised opening back by two years. The tug Sybill capsized and thirteen of her crew drowned. Roadbed on Stock Island, Boca Chica, and Sugarloaf washed out. On October 17 and 18, 1910, gusts reported at 110 miles an hour tore at the unfinished Seven Mile Bridge and at the track between the mainland and the Knight’s Key station. Meredith had already died, on April 20, 1909, in a Miami hospital, on the day the first steel span of that bridge was set. Krome, 32 years old and on the survey from the beginning, took the title of chief construction engineer and carried the work to Key West. A dynamite blast at the west end of Cudjoe Key in May 1909 had killed seven men and hurt seven more. The storms and the blasts were the price of the grade.

Knight’s Key

Flagler rode the first train from Miami to the Knight’s Key dock on January 22, 1908, across the new Long Key Viaduct, four years before the line would reach Key West. In February the railroad opened passenger service to that dock, and the Peninsular & Occidental steamer Montauk began a daily run from Knight’s Key to Key West and on to Havana. For the first time a rail passenger could change to a ship and be in Havana about six hours later. The machine shops went up on Boot Key, beside the camp that became Marathon, in April 1908. That fall Flagler opened the old workmen’s camp on Long Key as the Long Key Fishing Camp. Zane Grey was among the winter visitors who came to fish and to call it camping.

In January 1909 a luxury train left New York at 2:10 in the afternoon and reached Knight’s Key at 7:30 on the second morning. The dock was a terminal, with a steamer connection, while the bridges west of it were still piers in open water. Track reached Big Pine Key on June 30, 1909. Crews working east from Key West and west from Big Pine met on Sugarloaf Key in December 1911 and closed the last 27 miles. Flagler and Parrott made an inspection tour of Key West on December 16, 1911.

January 1912

On January 21, 1912 the engineers set the final steel plate girder on the Seven Mile Bridge. Before Flagler arrived, locomotive No. 201 tested the new track between Marathon and Key West. On January 22 the first Florida East Coast train into the city brought the 82-year-old builder and his wife, Mary Lily Kenan, in private cars 90 and 91, the train called The Rambler. The railroad’s own booklet dated the opening that day. The remark remembered from the platform is that his dream was fulfilled. On January 24, at 6:22 in the morning, The Rambler carried him north to Whitehall, his house at Palm Beach. It was his last visit to Key West.

The railroad had taken seven years, two years past the date Flagler had named in 1905. People who had doubted the line called it “Flagler’s Folly.” Once the trains were running, the same work was called the Eighth Wonder of the World. The cost was reckoned at about $50 million. On January 26 an excursion left Key West for Long Key with 123 passengers. The round-trip fare was $2.60. On February 8 the Key West Fish Company put its first shipment of iced fish on a train for New York.

Flagler died at Whitehall on May 20, 1913, at 83, and was buried at Memorial Presbyterian Church in St. Augustine. The extension outlived him by twenty-two years.

Trains and the Havana ferry

The traffic Flagler had promised was a mixture, and the mixture was thinner than the bridges. Passengers came, and so did fish, pineapples, and other keys produce, fresh water for the islands, and sealed freight for the port. The city he had counted on stayed small. The 1910 census gave Key West 19,945 people. The 1930 census gave it 12,831, while Miami, a hamlet when his railhead arrived in 1896, had 110,637. Cigars and sponges, the island’s old trades, had been moving to Tampa and Tarpon Springs. The coal stop for canal steamers, the reason most often given in 1905, faded as ships bunkered less often and as oil replaced coal.

What the extension did uniquely was the Cuba connection. In May 1912 the P&O advertised a five-dollar round trip from Key West to Havana on the Olivette and the Mascotte. A Havana newspaper that August printed a through timing: leave Havana at 10:30 in the morning, Key West at 6:30 in the evening, leave Key West at 7:30, Jacksonville at 1:55 the next afternoon, New York at 7:55 that evening, two nights on the way. The named train on the American side was the Havana Special. On January 8, 1915 the P&O car ferries Henry M. Flagler, Estrada Palma, and Joseph R. Parrott opened a freight service between Key West and Havana. Each ferry carried 26 railroad cars. The passenger trains south of Miami were few beside the main line farther north. They were steady enough that the January 2, 1930 Official Guide still printed them through Islamorada, Marathon, Bahia Honda, and Key West. The full system listing is the January 1930 Official Guide page.

Official Guide timetable of January 2, 1930, Florida East Coast main line continued south of Miami to Key West

Table 3 of the Official Guide of the Railways, January 2, 1930, page 647. The Florida East Coast main line continued south of Miami to Key West.

The parent railroad entered receivership on September 1, 1931. By then the extension was a long, expensive branch on the end of a bankrupt line: a passenger service, the car ferry, and a local freight. The Overseas Road and Toll Bridge District, created by the legislature in 1933, was already trying to finish a highway across the same water, and on February 16, 1931 motorists could drive to Matecumbe Key, ferry to Grassy Key, drive to Key Vaca, ferry again to No Name Key, and continue to Key West. The railroad and the unfinished road were both in the keys when the storm arrived.

September 2, 1935

The Labor Day Hurricane crossed the Upper Keys on the evening of September 2, 1935. The Weather Bureau’s barometer read 26.35 inches, and contemporary accounts put the wind at 200 miles an hour. It remains the most intense hurricane recorded at a United States landfall. Islamorada was wrecked. The National Weather Service estimates 408 deaths. A large share of the dead were World War I veterans living in Federal Emergency Relief camps on the keys, where they had been put to work on the highway. A relief train sent down from Miami reached Islamorada about 8:15 in the evening, as the surge arrived. The cars were swept off the rails. The locomotive stayed upright. The deaths were on the islands: people drowned, crushed, and carried into the mangroves. Bodies were recovered as far away as Flamingo and Cape Sable.

More than 40 miles of track went out, and two miles of it washed ashore at Cape Sable. The concrete viaducts and the steel bridges largely stood. The fill and the track between them were gone, including a gap of about two miles between Lower Matecumbe and Upper Matecumbe where the sea reopened a channel. The railroad, in receivership since 1931, left the extension unrepaired. A monument at Islamorada, beside the later highway, commemorates the civilians and the veterans killed that night.

The Overseas Highway

In 1936 the Florida East Coast petitioned the Interstate Commerce Commission to abandon what remained of the extension so a road could use the bridges. The Overseas Road and Toll Bridge District bought 122 miles of right-of-way, from Florida City to Key West, for $640,000 and the cancellation of $300,000 in state, city, and county taxes. On May 30, 1936 the Public Works Administration approved a $3.6 million loan for the work. On May 21, 1937 a federal judge authorized the receivers to sell the Trumbo Point terminal, aside from the Granday Turtle Canning Company, to S. C. Anderson of Coral Gables for $146,000. The Navy had taken the point for a seaplane station in 1917, while the railroad’s passenger yard, the one in the 1933 photograph, stayed in railroad hands until that sale.

Track came off the bridges and a roadway went on. Bahia Honda received its highway deck on top of the railroad trusses. Pigeon Key, mid-span on the Seven Mile Bridge, became a headquarters for the toll district. On March 29, 1938 a driver could go from the mainland to Key West and stay on the road the whole way. The toll at Lower Matecumbe was a dollar for the car and 25 cents for each passenger, with trucks charged from one to four dollars. Tolls came off in 1954. The car ferry to Havana, which had used the Key West dock, afterward left from Port Everglades and later from Palm Beach, and ran until 1960. That was a ship operation of the Florida East Coast’s successors in the steamship trade. The rails ended in 1935.

The original bridges carried automobiles until a new generation of spans replaced them. The new Seven Mile Bridge, 6.79 miles long, was formally opened on May 23, 1982, the last piece of a rebuilding that had begun in the late 1970s. On August 13, 1979 the National Register listed the Overseas Highway and Railway Bridges, covering the long survivors at Long Key, Knight’s Key, and Bahia Honda. In August 2004 the remaining historic railroad bridges were added. The old Seven Mile Bridge out to Pigeon Key, the Long Key viaduct, and the Bahia Honda trusses with the automobile deck still sitting on them are the extension a visitor can still walk or fish from. The through road beside them is U.S. 1, the Overseas Highway. The freight railroad that built the grade still runs from Jacksonville to Miami, and its later history is on the Florida East Coast page.

Sources

Florida East Coast Railway, Key West Extension (1912 booklet): Homestead to the Key West terminal, 128.4 miles; 17.2 miles of permanent bridge work, 11.1 miles of concrete-arch viaduct and 6.1 miles of steel on concrete piers; Bahia Honda foundations 30 feet below tide; 134 acres of fill; pier 1,700 by 134 feet. The booklet dates the opening January 22, 1912.
Key West Art & Historical Society, Flagler Overseas Railway Timeline: the construction log from the April 29, 1893 charter through January 1912, including Meredith’s death on April 20, 1909, cars 90 and 91, the 1909 and 1910 hurricanes, the car ferries of January 8, 1915, and the highway dates of 1936–1938.
“The Florida Overseas Railroad,” Florida Historical Quarterly, vol. 35, no. 4 (1956): Meredith’s hiring, the engineering staff, Parrott and Flagler, Long Key Viaduct at 2.68 miles and 180 arches, the October 1906 hurricane and houseboat No. 4, and a count of 130 dead.
National Park Service, National Register nomination, and Florida State Parks, “The Flagler Railroad”: Seven Mile Bridge at 35,815 feet, Bahia Honda at 5,055 feet, more than 4,000 men, the 1979 and 2004 Register listings. Register reference 79000684, added August 13, 1979.
National Weather Service estimate of 408 deaths, and the Weather Bureau pressure of 26.35 inches. Willie Drye, National Geographic, September 8, 2017, for the relief train at Islamorada about 8:15 p.m. and the locomotive left upright. Hurricane accounts for more than 40 miles of track destroyed, two miles of it ashore at Cape Sable.
Tequesta (Historical Association of Southern Florida, 1986): the 1936 purchase of 122 miles for $640,000 and cancellation of $300,000 in taxes; March 29, 1938, the ferry-free road; tolls removed in 1954; new Seven Mile Bridge formally opened May 23, 1982.
U.S. Census: Key West, 19,945 in 1910 and 12,831 in 1930; Miami, 110,637 in 1930.
Seth H. Bramson, Speedway to Sunshine (Boston Mills Press, 1984) and The Greatest Railroad Story Ever Told (The History Press, 2011), the book-length histories of the railroad and the extension.
Railway Wonders of the World, for the 15-mile-an-hour restriction on the viaducts. Invention & Technology, “The Railroad That Went to Sea,” for Meredith’s remark after the 1906 storm.

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