- The Things I've Seen
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- TIS-003 - On the Overseas Railroad, or at least alongside it
TIS-003 - On the Overseas Railroad, or at least alongside it
The Things I’ve Seen
“I did not tell half of what I saw, for I knew I would not be believed.” - Marco Polo on his deathbed, 1324, apparently? Uncharted said so.
“I have discovered a truly marvelous proof of this, which this margin is too narrow to contain.” Pierre de Fermat, though that was about maths.
I’m one of today’s lucky 10,000: https://xkcd.com/1053/
The drive down to Key West (and back again) was a real privilege. It's a wonderful scenic ride, provided traffic is cooperative. One of the wonders is how the roads and bridges were initially built to get cars to Key West. The Keys are unfriendly terrain to efforts to connect them, and sadly, many techniques to connect them were unfriendly to the Keys in return. Before cars, Henry Flagler, a Standard Oil co-founder and train enthusiast, first connected the mainland to the Keys by rail. To me this makes it even more interesting that Hemingway originally visited Key West with his then wife Pauline Pfeiffer to pick up a Model T ford that her Uncle Gus had purchased as a wedding gift. The Pfeiffers were That Kind Of Rich, owning a pharmaceutical company (Pfeiffer Pharmaceutical, later acquired by S.S.S.). When the car was delayed due to ferry issues, as the roads didn't get all the way there yet, Uncle Gus bought them a seashore house. Instead of ferrying back, they stayed and settled. Dredging and landfill has moved it back from the shore, but the Hemingway Pfeiffer house is a story for another issue. For now, I saw the Overseas Railroad and read Last Train to Paradise by Les Standiford, so you'll get that story this week.
The Overseas Railroad
To continue the unexpected theme for today, Flagler was another rich man. Financial comparisons are hard, but we can safely say he'd be in what we'd consider the billionaire category today. Standard Oil made him rich, and his hobby of creating and connecting resorts supercharged his wealth. I sound flippant, but he founded the Florida East Coast Railway to build a railroad along the East coast of Florida to places he thought were pretty cool and would sustain a luxury resort which he would also build. Towns were connected almost incidentally, it seems like. West Palm Beach was originally the end of his ambitions. Then a series of freezes in the 1890s killed produce like the famous Florida oranges. Julia Tuttle, founder of Miami which survived the freeze, allegedly sent one of Flagler's men back from a business visit with a basket of orange blooms. The message was "hey, would be a shame if a frost-tolerant up and coming city got a railroad and a resort." Flagler continued his rail, putting him that much closer to Key West. Then, he became a man obsessed with finishing the job. It was a venture that wouldn't bankrupt him, but it definitely demonstrated his resolve and destroyed his company by the end of it. He lived to see the Overseas Railroad get to Key West, but not to see the Overseas Railroad destroyed and the company bankrupted in the Labor Day Hurricane of 1935.
The story is fascinating. Flagler had finished his railroad ambitions when he stopped at West Palm Beach. Then Julia Tuttle convinced him to unfinish them because of some citrus fruit. With Key West now his goal, he had a lot to do and he wasn't getting any younger. The project was massive, bringing in workers (under dubious premise) from all across the East coast. Liquor was prohibited, but shanty towns and offshore pleasure barges filled the void. Few foremen were willing to strictly enforce the rules, so the prohibition was more a paper thing. This fast and loose approach was devastating when hurricanes arrived. The worst documented case was on October 17, 1906, when a storm took the lives of between 125 to 200 men. The low estimate of 125 was about 5% of the work force. After such a material impact to his progress, Flagler insisted on better, safer accommodations for his workforce and improved evacuation protocols. The company seemed to act like hurricanes were surprising to them, though one of his chief builders, Krome, had said on multiple occasions they knew how bad things were and ignored them until terrible things happened. Between the hiring and labor practices and storm dangers, apparently Flagler ran afoul of President Theodore Roosevelt. "I have no command of the English language that enables me to express my feelings regarding Mr. Roosevelt," he once wrote. "He is shit." 1
On January 21, 1912, 7 years after it started, construction was considered complete. The railroad ran until its unrecoverable destruction in 1935, a mere 23 years later. Its short run was not in vain, though. In the 1920s-1940s (the timeline is unclear to me, but I didn't really dig in) there was a dedicated effort to connecting the Keys by road. This was State Route 4A, which eventually made its way to Lower Matecumbe Key and No Name Key, but not between. Instead, you and your car would take a 41 mile ferry ride, provided the ferry was in good service. Auto enthusiasts could not afford the massive undertaking, but when the State of Florida fell into possession of the Overseas Railroad railbed and right of way, the project became a lot more feasible. 7 Mile Bridge and the Bahia Honda bridge were critical pieces of infrastructure to restore, making a complete Route 4A possible. Eventually State Route 4A was granted designation as part of US Route 1, and over time was realigned, then unaligned with the Overseas Railroad path. OpenStreetMaps will show you how it winds around, crossing keys at what were determined to be the points of least resistance to Flagler's crews over a hundred years ago.
![]() Begin | ![]() End |
It also shaped the growth of Key West, quite literally. The major source of fresh water until the Overseas Railroad was cisterns that collected rainfall. The Overseas Railroad changed that, as one of its biggest impacts was regular water service. When the Overseas Railroad was destroyed in 1935 and sold off to the State, a town now dependent on rail transport of water was in a real hard place. By 1937 the Florida Keys Aqueduct Commission was put together, and soon after as World War II was evolving, the U.S. military backed water pipelines to Key West. It was a strategic point on the U.S. coast and a notable port of its own right with a significant naval presence, but again, not today’s story. I haven't tried to trace a path through, but the current iteration, the Florida Keys Aqueduct Authority, sits smack dab in the middle of the action of Old Town Key West, piping water from if I recall correctly as far away as Fort Myers. Wow.

Water, water everywhere…and these drops you can drink!
7 Mile Bridge
7 Mile Bridge is a really cool section of the Overseas Railroad, then Overseas Highway, then pedestrian bridge, then scenic stop and fishing pier, and potentially in the next few years part of the Florida Keys Overseas Heritage Trail (currently marked as closed footpath, seek alternate route). Like much of the rest of the Overseas Railroad, it's a testament to Humanity's dedication to connecting the Keys. Ever Becoming, with its builders always confident in its Being. It's not Platonic, but people have been infected with a Flagleresque drive to make it solid.
![]() We do not do these things because they are easy. We do them because they’re heckin’ fun and we can put our names on them. | ![]() The approach from Little Duck Key. |

Little Money Key, sitting out there earning.
At its time, it was one of the longest bridges ever built, and was built in unfriendly terrain. The base had to be dredged of "muck" to find limestone, which sometimes was quite thin and over sand, requiring further piledriving and digging to ensure stability. You weren't really sure what you would find on any given pier. divers set up cofferdams, which were pumped dry to set piers with submarine concrete, and a different concrete was used above water. iron, wood, aggregate...all kinds of supplies, all had to be shipped in. It was a massive project, and I'll leave it at that. Work on this bridge alone ran from 1909-1912, 3 of the 7 years of the entire Keys project. It was also the last piece finished.
And yet, the work still wasn't done. Bridges need to be painted to protect their structure from the elements. The paint that could protect bridge materials at this time from the harsh salt environment would only last two years. For the life of the railroad, repainting 7 Mile Bridge was a full-time job. Once a fresh coat of paint was finished, it was time to start again. Even still, even after 1935 and the collapse of the Florida East Coast Railroad, the Overseas Highway itself not only used the bridge deck, they pulled up the rails to use as the original guardrails. Concrete rails now line the path, but the original guardrails (and the still narrow width of the road) are visible today.
![]() Where the sidewalk ends. The original rails still hang off the edges. This was a road. That you would drive on. | ![]() US 1, right nearby. |
Today you can walk about 2 miles of the bridge. On the west end of Marathon, there's a small overlook park. From there the Overseas Railroad/Highway will take you to Pigeon Key, about 2 miles away. I did not check that out, which goes to show that even with all the things I've seen, there's still opportunities to see more. On the west side of the bridge is Little Duck Key, which has a free access lot with a boat launch and maybe a half a mile of the original bridge set up as a fishing pier. Little Money Key is immediately to the North, and Money Key is to the South across the new US 1.
After those walking sections, the bridge has had spans removed to keep people off of the rest. There was also a turntable removed at Moser Channel, which was used to allow taller ships to pass. This is particularly neat because it looks like this was the last section of the railroad to be completed. You can drive right past the gap today, and really, it's hard to miss. The best record I could find on this was from the National Park Service in a Historic American Engineering Record 2 .
When the last 80-ft. steel girder was set by derrick barge No. 9 at 6:00 a.m., January 21, 1912, and when the last rail was laid at Span 36 in the Knight's Key Bridge late that Sunday afternoon, and when the last spike was driven in the early morning of January 22, 1912, the span was announced completed by Division Engineer C.S. Coe at 6:30 a.m. This was the span closing the gap over the Knight's Key trestle and thereby completing the Key West Extension of the Florida East Coast Railway. The pilot train and the Flagler Special ran over the bridge and on to Key West a few hours later (1).
Footnotes (1) Carleton J. Corliss, Historical Notes of the Key Vaca Area and Marathon, FEC Collection, Henry Morrison Flagler Museum, Palm Beach, Florida (typewritten).

Fred the Tree (and his younger brother).
While the 7 Mile Bridge is closed to people, nature fears no courts of law and refuses to bind itself to our civic artifices. Fred the Tree and his younger brother have taken up root (literally) on the west end of the 7 Mile Bridge, not too far from the fishing pier. You get a great look at him on the way out. Fred looks like a pine, but apparently it's an Australian Pine which isn't a true pine. Naming is hard, I guess. Anyway, that's pretty cool! It was wild to see such tenacity just hanging out, both on the part of Fred and on the bridge. While unsound for traffic, you can still see it standing today, refusing to give in to gravity’s inexorable beck.
Bahia Honda Bridge
Starting in the Bahia Honda State Park, on Bahia Honda Key, the Bahia Honda Bridge crosses the Bahia Honda Channel. It was built in a spot where the bridge would only need to be about a mile long, seemingly a slam dunk after 7 Mile Bridge. The channel had some of the deepest waters of the project, though, some 20-35 feet deep in places. This bridge was also built near the end of the project, after several hurricane-related disasters taught some valuable lessons. The team learned a general rule: build up one foot for every one foot of water below, to avoid the worst of the hurricane surges. That made this the tallest bridge along the Overseas Railroad, and all that extra height added even more engineering work. If you are used to seeing other pictures from the Overseas Railroad, this bridge might stand out a bit. I was surprised to see so much structure, and assumed other bridges had originally looked like that, until I dug further.
![]() Do not pass go. | ![]() The Western approach. |
The Bahia Honda bridge still stands, with sections taken out on either side to prevent people like me from going out and having a little adventure. You can still approach it from either side, though. There’s even a short section from Loggerhead Beach that’s still walkable, as I understand it. From the west approach, you can only look at the old bridge from land. This is one part of US 1 that does not follow the Overseas Railroad anymore, which now opts for a slightly longer but more direct path. The Bahia Honda Bridge was a part of the Overseas Highway for a while, which came with its own problems. The rail deck inside the truss wasn't wide enough for vehicular traffic, unlike the rest of the Overseas Railroad, so a roadbed was built over the truss. It's really clear when looking at historical pictures of the Overseas Railroad: extra vertical trusses that wouldn't have been there for the original spans, and the extra deck on top. You can even see the guardrails.

Build up.
I would love to see this be part of the Florida Keys Overseas Heritage Trail, but as far as I can tell that's not part of the plan. Instead, some signs have been hung warning boaters to watch out for falling debris. It hasn't fallen over yet, so it's still a thing you can see as well. You can even set foot on it at Bahia Honda State Park - just head to Loggerhead Beach, and keep going West. If your feet get wet, take another look.
Until Next Time
There's more Key West to talk about, though if anything really cool comes up or I feel like taking an interstitial to write about something else, well, that might happen. There's so much still to cover: restaurants, the US CGC Ingham, forts, the Little White House...so much more! Even older things, that have survived even longer! Until next time, I'll see you on the Internet.
1 Last Train to Paradise - Page 136
2 The original quote was on page 4 of the Historic American Engineering Record. I’ve seen references to Knights Key, but this is the most precise description of the Railroad’s completion I found in my admittedly cursory search.
Thanks! Here’s all the beehiiv stuff that is required to be here
— Lou







