From the archives

Islamorada, remembered in photographs

Rail, road, storm, and sea shaped the Upper Keys. These ten images preserve moments from that story, with special attention to Islamorada and its neighboring islands.

A house destroyed in the Upper Florida Keys after the 1935 Labor Day Hurricane — A building destroyed after the 1935 Labor Day Hurricane. Florida Keys History Center, Monroe County Public Library; CC BY 2.0.

The Long Key Fishing Club building on Long Key, Florida, about 1919, with an inset view of the Long Key Viaduct — **Long Key Fishing Club, about 1919**Henry Flagler's railroad built this fishing camp on Long Key, and it drew anglers — Zane Grey among them — from across the country. The 1935 hurricane destroyed it.State Archives of Florida, Florida Memory; public domain.

A Florida East Coast Railway express train crossing the Long Key Viaduct between 1912 and 1935 — **An express train at sea, 1912–1935**A Key West Extension train crosses the Long Key Viaduct. For twenty-three years this was how people and freight reached the Keys.Key West News Co.; State Archives of Florida, Florida Memory; public domain.

Florida Keys concrete railroad viaduct beside an early Overseas Highway bridge in 1932 — **From rail to road, 1932**A concrete Florida East Coast Railway viaduct runs beside an early Overseas Highway bridge — the two eras of Keys travel side by side.Photograph by Jesse S. Wooley, Floyd and Marion Rinhart Collection, University of Miami Libraries; No Copyright—United States.

The wrecked Islamorada Moose Lodge after Hurricane Donna in September 1960 — **After Hurricane Donna, September 1960**Donna crossed the Middle and Upper Keys as a major hurricane. The Islamorada Moose Lodge was left in pieces, its sign still standing.Photograph by Bernard M. (Buzz) Cooper and Doris V. Cooper; Florida Keys Public Libraries; CC BY 2.0.

Islamorada Mimeo and Photo Service storefront on Upper Matecumbe Key in December 1964 — **Islamorada Mimeo & Photo Service, 1964**A working storefront on Upper Matecumbe Key, photographed by the county Property Appraiser's office — an accidental record of everyday island business.Florida Keys Public Libraries; CC BY 2.0.

The Islamorada Chamber of Commerce building with a telephone booth outside, about 1965 — **Islamorada Chamber of Commerce, about 1965**An Information arrow, a pay phone, and a hand-lettered sign: how visitors found their way around Islamorada before the internet.Florida Keys Public Libraries; CC BY 2.0.

The Monroe County Public Library branch in Islamorada on Upper Matecumbe Key, about 1965 — **The Islamorada library, about 1965**The Monroe County Public Library branch on Upper Matecumbe Key. Local history collecting in the Upper Keys has deep roots.Florida Keys Public Libraries; CC BY 2.0.

Former President Herbert Hoover with Upper Keys fishing guide Calvin Albury at a Key Largo dock in 1956 — **A president and his Upper Keys guide, 1956**Former President Herbert Hoover with Calvin Albury, the guide who took him fishing in Upper Keys waters for more than a decade.Herbert Hoover Presidential Library; U.S. government work.

In our online collections

See more photos

These ten photographs are just the beginning. Browse our full digitized collections online — historic images, artifacts, and documents from the Center's holdings, available anytime.

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Aerial view of Indian Key showing the historic island beside the Overseas Highway near Islamorada

Then & now

Indian Key from above

This modern aerial view reveals the footprint of a much older community. Indian Key became the county seat of Dade County in 1836, and traces of its streets and building foundations remain visible today just offshore from Islamorada.

Explore the Indian Key exhibit →

National Scenic Byways Program / National Archives; public domain.

Sources & stewardship

Every image carries a history

Dates, places, and credits follow the holding archives. Some locations are identified broadly as the Florida Keys when the original record is not more specific. We welcome corrections and photographs that can help document Islamorada's past.

Have an Islamorada photograph or story to share? Email info@keysdiscovery.com.

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