Short answer: Henry Flagler began buying and building railroads on Florida's Atlantic coast in 1885, reached Miami by 1896, and pushed his Florida East Coast Railway across the Keys to Key West, where the first train arrived on Jan. 22, 1912. He built hotels along the way, including the Hotel Ponce de Leon of 1888. After the 1935 Labor Day hurricane the Keys line was sold to the state and Monroe County, and 23 of its bridges now carry a heritage trail.
Last verified: October 18, 2026, against the sources listed at the end of this page.
What was the Flagler era of Florida railroads?
Henry Flagler began building up a railroad system on Florida's Atlantic coast in 1885, and by 1912 he had extended it across the Florida Keys to Key West (State Archives of Florida).
The State Archives summarizes the arc in three dates: Flagler bought existing lines and built new track from 1885, reached as far south as Miami by 1896, and extended the road across the Florida Keys by 1912 (State Archives). He founded what became the Florida East Coast Railway, running its lines through Jacksonville and down the east coast during the 1880s and 1890s (Florida Memory teacher guide).
State policy set the stage. The Department of State traces Florida's transportation growth to the Internal Improvement Act of 1855, which offered investors cheap or free public land, and says the act had its greatest effect between the Civil War and World War I, when companies owned by Flagler and Henry B. Plant built many railroads and lavish hotels beside them (Department of State). Last verified: October 18, 2026, against five State Archives railroad pages, the Department of State development chapter, and three Florida State Parks pages on the Keys line, including the current trail closures.
Why did Henry Flagler invest in Florida?
In his own words, by chance: in a March 20, 1902 letter held at the State Archives, Flagler wrote that his first investment in Florida was simply the outcome of a casual visit (State Archives, Flagler letter).
The letter, written from Palm Beach on Hotel Royal Poinciana letterhead to Ellen Call Long, daughter of territorial governor Richard Keith Call, says his attention was first drawn to the upper east coast and that he later saw the possibilities of the section in its soil and climate. He closed by saying he had unbounded faith in the resources of the state and its citizens (State Archives). The Bahia Honda State Park history page says the dream of the Bahia Honda Bridge began with Flagler's first trip to Florida in 1878 (Florida State Parks).
The timing fit a statewide rail expansion. The State Archives photo exhibit says that after Plant built lines to Tampa and the west coast and Flagler built down the east coast in the 1880s, railway mileage in the state increased four-fold that decade, and that the State Railroad Commission, established ten years earlier, grew stronger in 1897 to regulate passenger and freight rates (Florida Memory exhibit).
Which Flagler hotels and estates still stand?
Two Flagler landmarks remain in use: the Hotel Ponce de Leon in St. Augustine, now Flagler College, and Whitehall in Palm Beach, now the Flagler Museum (State Archives; Flagler Museum).
A State Archives photograph record says Flagler built the Hotel Ponce de Leon in St. Augustine, Florida, and opened it in 1888; it closed in 1967 and was sold to Flagler College, joined the National Register of Historic Places in 1975 and became a National Historic Landmark on February 21, 2006 (State Archives photo record).
Whitehall, Flagler's Palm Beach estate, is open to the public as the Flagler Museum, which offers self-guided tours, changing exhibitions and special programs. The museum is at One Whitehall Way, Palm Beach, phone (561) 655-2833 (Flagler Museum). The Department of State notes that both Flagler and Plant built lavish hotels near their railroad lines (Department of State).
How was the Overseas Extension to Key West built?
The Overseas Extension carried the Florida East Coast Railway from Miami across the Keys to Key West, where the first train arrived with Flagler aboard on Jan. 22, 1912 (Florida State Parks).
Florida State Parks says Flagler decided to extend the line after construction of the Panama Canal began, that many engineers told him it could not be done, and that project engineer James Meredith shared his vision. The work took 7 years, over $50 million and 17 million cubic yards of material placed on the right-of-way; more than 4,000 men were working at any given time, and three hurricanes crossed the Keys during construction (Florida State Parks).
| Event | Date given | Source |
|---|---|---|
| Construction begins | 1906 | State Archives teacher guide |
| Construction begins | 1906 | State Archives photo exhibit |
| Construction begins (the park page calls the project the Florida Keys Overseas Highway, connecting Miami to Key West) | 1904 | Bahia Honda State Park history |
| First train enters Key West | Jan. 22, 1912 | Bahia Honda State Park history |
| Overseas Highway opens on the old route | 1938 | Florida State Parks |
The state sources disagree on the start year, as the table shows, and give no single date. Engineering varied along the route: at Bahia Honda, the park says, extreme water depth led engineers to use steel trusses instead of the concrete arches seen elsewhere on the line, and the work was dangerous, with many laborers losing their lives to heat, hurricanes and disease (Florida State Parks).
What happened to the Key West railroad after the 1935 hurricane?
The Labor Day hurricane of 1935 ended rail service to Key West; the railroad sold the line to the State of Florida and Monroe County for $640,000, and the Overseas Highway opened on it in 1938 (Florida State Parks).
Two Florida State Parks pages describe the damage differently. The Flagler Railroad page says the storm, with winds estimated at 200 mph, left some damage but the railroad remained mostly intact, and that high building and upkeep costs drove the sale (Florida State Parks). The Bahia Honda history page says parts of the line were significantly damaged for the first time since completion and that repairs took several years, and that rather than abandon the Bahia Honda bridge the state bought it to include in the conversion of the railway into a highway (Bahia Honda history).
The old bridges gained protection in stages. Florida State Parks says that in 1979 the Long Key Channel, Knight's Key (7 Mile) and Bahia Honda Channel historic railroad bridges were listed on the National Register of Historic Places; a task force formed in 1997 to preserve the bridges for pedestrian and recreational use; and in August 2004 the remaining 20 historic railroad bridges and the Overseas Highway were listed too (Florida State Parks).
How did Flagler's railroad change Florida?
Rail lines like Flagler's brought tourists to Florida, carried citrus north to market in less than a week, and helped found new towns along the tracks (State Archives; Department of State).
The State Archives says trains such as the Florida Special and the Orange Blossom Special brought tourists to Miami and beyond in the early 20th century, and that railroads helped establish new towns and served the lumber, phosphate, tourist, manufacturing and agricultural industries (Florida Memory). The Department of State points to citrus: rail made it possible to pick oranges in south Florida and eat them in Baltimore, Philadelphia or New York in less than a week (Department of State).
The State Archives says that by 1912 the Florida East Coast Railway Company had completed the first railroad connecting Key West with the mainland (Florida Memory).
Where can the Flagler railroad be seen today?
In the Keys, the Florida Keys Overseas Heritage Trail incorporates 23 of the historic Flagler Railroad bridges (Florida State Parks).
The trail has more than 90 linear miles paved in segments along a planned 106-mile corridor from Key Largo to Key West, beside U.S. Highway 1. It is open 8 a.m. to sunset with no fee; the administrative office is at 3 La Croix Court, Key Largo, phone 305-853-3571. Anglers should know that the park lists the Ohio-Missouri, Ohio-Bahia Honda, Missouri-Little Duck, Lower Sugarloaf and Niles fishing bridges as closed for safety (Florida State Parks).
At Bahia Honda State Park, the old Bahia Honda bridge now serves as an overlook (Florida State Parks). On the mainland, the former Hotel Ponce de Leon belongs to Flagler College in St. Augustine (State Archives), and Whitehall in Palm Beach is open as the Flagler Museum (Flagler Museum). The State Archives railroad photo exhibit includes a 1912 photograph of Flagler getting off the train at Key West for the official opening of the extension (Florida Memory exhibit).
Frequently asked questions
When did Flagler's railroad reach Key West?
The first train entered Key West on Jan. 22, 1912, with Henry Flagler aboard, according to Florida State Parks. He died the following year.
When did construction of the Overseas Extension start?
State sources differ. Two State Archives of Florida pages say Flagler began the Overseas Extension in 1906, while the Bahia Honda State Park history page, in its section on building the railroad, says construction of what it calls the Florida Keys Overseas Highway, connecting Miami to Key West, began in 1904.
Why did the Overseas Railroad stop running?
The Labor Day hurricane of 1935 hit the line, and the railroad sold it to the State of Florida and Monroe County for $640,000, Florida State Parks says. The Overseas Highway opened on the route in 1938.
Can people walk or bike the old Flagler bridges?
Yes. The Florida Keys Overseas Heritage Trail uses 23 historic Flagler Railroad bridges, is open 8 a.m. to sunset and charges no fee, though Florida State Parks lists five fishing bridges as closed for safety.
What is the Hotel Ponce de Leon today?
The hotel Flagler opened in St. Augustine in 1888 closed in 1967 and was sold to Flagler College. It became a National Historic Landmark on February 21, 2006, according to a State Archives record.
Sources
- Florida Memory (State Archives of Florida), Letter from Henry Flagler (1902) https://www.floridamemory.com/learn/classroom/learning-units/railroads/documents/flagler/ Used for: Flagler began building a railroad system on the Atlantic coast in 1885; as far south as Miami by 1896; Key West by 1912; letter dated March 20, 1902 from Palm Beach on Hotel Royal Poinciana letterhead; first investment the outcome of a casual visit
- Florida Memory (State Archives of Florida), Teacher's Guide for Henry Flagler in Florida https://www.floridamemory.com/learn/classroom/learning-units/railroads/lessonplans/guides/flagler/ Used for: Flagler founder of what became the Florida East Coast Railway; lines through Jacksonville to Miami in the 1880s and 1890s; Overseas Extension begun 1906
- Florida Memory (State Archives of Florida), Railroads Change Florida overview https://www.floridamemory.com/learn/classroom/learning-units/railroads/ Used for: first Florida train 1836; Plant to Tampa and Flagler down the East coast in the 1880s; Key West line by 1912; Florida Special and Orange Blossom Special; towns and industries
- Florida Memory (State Archives of Florida), Tracks Toward the Future photo exhibit https://www.floridamemory.com/learn/exhibits/photo_exhibits/trains/ Used for: railway mileage increased four-fold in the 1880s; State Railroad Commission strengthened 1897; Overseas Extension begun 1906; Flagler at Key West 1912; Fort Pierce engines 29 and 30
- Florida Memory (State Archives of Florida), Hotel Ponce de Leon photograph record https://www.floridamemory.com/items/show/64631 Used for: built by Flagler, opened 1888; closed 1967 and sold to Flagler College; National Register 1975; National Historic Landmark February 21, 2006
- Florida Department of State, Florida Development https://dos.fl.gov/florida-facts/florida-history/a-brief-history/florida-development/ Used for: Internal Improvement Act of 1855 offered cheap or free land; railroads by Flagler and Plant companies with lavish hotels; citrus by train to northern cities in under a week; tourists from the 1870s
- Florida State Parks, The Flagler Railroad https://www.floridastateparks.org/learn/flagler-railroad Used for: Panama Canal motive; engineer James Meredith; 7 years, over $50 million, 17 million cubic yards; more than 4,000 men; three hurricanes; complete 1912; Labor Day hurricane 1935; sold for $640,000; Overseas Highway 1938; National Register 1979 and August 2004
- Florida State Parks, Bahia Honda State Park history https://www.floridastateparks.org/parks-and-trails/bahia-honda-state-park/history Used for: Flagler's first Florida trip 1878; construction began 1904; steel trusses at Bahia Honda; dangerous work; first train to Key West Jan. 22, 1912; 1935 damage; state bought the bridge
- Florida State Parks, Florida Keys Overseas Heritage Trail https://www.floridastateparks.org/parks-and-trails/florida-keys-overseas-heritage-trail Used for: more than 90 miles paved along a 106-mile corridor; 23 historic Flagler Railroad bridges; closed fishing bridges; 8 a.m. to sunset; no fee; 3 La Croix Court, Key Largo; 305-853-3571
- Henry Morrison Flagler Museum (own facts) https://www.flaglermuseum.us/ Used for: Whitehall completed 1902; National Historic Landmark open as the Flagler Museum; One Whitehall Way, Palm Beach; (561) 655-2833
How this page was made
Digital Towns uses AI assistance to research and write its guides, and every page is only as good as the sources it cites. Our goal is the most accurate, useful local information possible.
This page was fact-checked twice before publishing.
If you see an error, or anything you can show is false, tell us right away and we will take a third look.
Report an error
Thank you. We'll take a third look and correct the page if it's wrong.
