Hurricane Risk in Islamorada, Florida
The Florida Keys hub page on this site covers the chain-wide facts that apply to every community here -- the single-highway evacuation route and the way growth-control law (ROGO/NROGO) is built around hurricane-evacuation capacity. This page doesn't repeat that. It covers what's specific to Islamorada: the Category 5 Labor Day Hurricane of September 2, 1935 struck the Islamorada/Matecumbe Keys stretch directly, and it remains the single most consequential storm in this community's history -- not just as history, but as the reason a serious amount of today's evacuation infrastructure and the Overseas Highway itself exist. None of what follows is a substitute for a property-specific evacuation-zone check, a conversation with Monroe County Emergency Management, or advice from a Florida-licensed insurance professional before you buy, insure, or ride out a hurricane season here.
September 2, 1935: The Storm That Hit Islamorada Hardest
The Labor Day Hurricane of 1935 was a Category 5 storm at landfall, and it came ashore directly across the Islamorada/Matecumbe Keys stretch of the chain -- Upper and Lower Matecumbe Key, now part of the Village of Islamorada. Of everywhere along the Florida Keys the storm touched, this is the ground it hit hardest, and the concentration of death here was the highest anywhere along the chain.
The reason so many people were in harm's way on these specific islands is itself part of the story: the federal Emergency Relief Administration (FERA) was running work camps here at the time, employing World War I veterans on construction of the Overseas Highway extension -- the same highway project that today carries every resident and visitor off the Keys ahead of a storm. Those camps sat exposed on low, narrow islands with no fixed shelter built for a storm of this intensity.
The Rescue Train and the 166-Veteran Figure
As the storm's severity became clear, a rescue train was dispatched from Miami to evacuate the veterans and other residents off the islands. It arrived too late: the storm surge swept the train from the tracks before it could complete the evacuation. That single event -- a rescue effort overtaken by the storm itself -- is one of the most documented and cited moments of the entire 1935 hurricane.
On the specific human toll, this page states one figure and one figure only, because it is the one this research could independently source: the U.S. Department of Veterans Affairs has cited, in one of its own 'Veteran of the Day' posts, a figure of 166 veterans killed in the storm. This page does not state a broader Keys-wide or Islamorada-total death toll beyond that specific veteran figure -- a wider total is commonly repeated elsewhere, but it could not be independently confirmed against a primary source in the research behind this page, and the two numbers should not be conflated. If you want a verified overall total, NOAA's and the National Hurricane Center's historical storm archives are the right place to look before relying on a number you see quoted elsewhere.
Hemingway's "Who Murdered the Vets?"
Ernest Hemingway was living in Key West at the time of the storm, and in its immediate aftermath he sailed to the Upper Keys to see the damage himself. What he saw led him to write one of the angriest pieces of his career: "Who Murdered the Vets?", published in The New Masses on September 17, 1935 -- a first-person essay indicting the federal government for failing to evacuate the veterans' work camps in time, despite the storm's approach being known well in advance.
This is a real, documented, citable piece of writing, not a footnote or a rumor -- it survives in reprint and has been the subject of independent historical retrospectives. It's also a genuinely distinctive fact for anyone researching this community: a Nobel laureate's own furious, on-the-record account of a disaster that struck the exact ground Islamorada now sits on, written within two weeks of the storm.
1935 to Today: Why This History Isn't Just History
The Florida Keys hub page on this site covers, in detail, how the modern Overseas Highway and the single-road evacuation reality it creates shape hurricane policy across the entire chain today. What's worth stating plainly on this page is the direct line between that infrastructure and the 1935 storm: the veterans killed in the Labor Day Hurricane were building the very highway extension that, in its rebuilt and expanded form, is now the region's only evacuation route off the islands. Modern evacuation planning and the road itself exist, in part, because this exact disaster happened on this exact stretch of the Keys.
That's the honest way to connect the history to a present-day buying decision: this isn't a community with an abstract, generic hurricane risk. It's a community where the worst storm in Keys history hit the ground it's built on, killed a specific and citable number of the workers building its road, and produced a still-read piece of American writing calling out the government response -- and where the infrastructure built in that storm's wake is the same infrastructure you'd be relying on to leave before the next one.
The Practical Takeaway
Islamorada's hurricane history is not generic Keys trivia -- it's a specific, well-documented catastrophe that struck this exact stretch of islands, killed a citable number of the veterans building the road this community still depends on, and produced Hemingway's own furious, on-the-record account of the government's failure to get people out in time. For the chain-wide facts that apply to Islamorada alongside every other Keys community -- the single-highway evacuation route and how ROGO/NROGO growth caps function as hurricane policy -- see the Florida Keys hub's own hurricane-risk page.
None of this history substitutes for property-specific diligence or real-time emergency guidance. This page is not insurance, legal, engineering, or emergency-management advice. Before buying, insuring, relocating to, or riding out a hurricane season in Islamorada, confirm the property's current FEMA flood zone and evacuation zone directly with Monroe County and the Village of Islamorada, ask Monroe County Emergency Management for current evacuation-clearance-time and shelter guidance, and talk with a Florida-licensed insurance professional about wind, flood, and hurricane-deductible coverage.
Ready to talk to a local Islamorada agent?
Get a Free Agent Referral →Independent research. No ads. No sponsored listings. The Category 5 Labor Day Hurricane's September 2, 1935 landfall directly across the Islamorada/Matecumbe Keys stretch, the highest concentration of storm deaths anywhere along the chain, the presence of WWI veterans in FERA work camps building the Overseas Highway extension, and the rescue train swept from the tracks by storm surge are drawn from the Library of Congress/Florida Memory's 'Rescue Train Swept off the Tracks' item, Britannica's 'Labor Day hurricane of 1935' entry, and NOAA AOML's 80th-anniversary retrospective. The 166-veteran death figure is drawn specifically from a U.S. Department of Veterans Affairs 'Veteran of the Day' post; this page does not state, and did not independently confirm, any broader Keys-wide or Islamorada-total death toll beyond that specific figure, and the two should not be conflated. Ernest Hemingway's 'Who Murdered the Vets?', published in The New Masses on September 17, 1935, is confirmed via a full reprint and independent retrospectives from History News Network and The Conversation. This page did not confirm a specific current evacuation-clearance-time figure, flood-insurance premium, or FEMA flood-zone designation for any Islamorada property -- confirm those directly with Monroe County, the Village of Islamorada, Monroe County Emergency Management, and a Florida-licensed insurance professional before making any purchase, insurance, relocation, or preparedness decision. Nothing on this page is legal, insurance, engineering, or emergency-management advice.