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Islamorada Information and History

by local historian, Irving R. Eyster

Today's Islamorada area extends from the Long Key bridge on the southwest to Tavernier Creek on the northeast, encompassing Long Key, both Matecumbes, Windley and Plantation Key. The Upper Keys were formed nearly 100,000 years ago by corals building a reef. This formation can be clearly seen today at the Windley Key Quarry Geologic State Park.

Indians lived on these islands almost 4,000 years ago. The first recorded history was by Ponce de Leon who sailed through the Keys in 1513. He called them Los Martires. A map of the time indicated an island known as Guarugumbe in this section of the Keys. The Indian name was corrupted by the Spanish into Matecumbe which has survived to this day.

In 1733, a hurricane destroyed almost the entire Spanish treasure fleet as it returned to Spain. Most of the remains of this fleet can be seen on the Islamorada reefs. One ship, the San Pedro, is now an underwater state park.

The first permanent settlers came to the area from the Bahamas in the 1800's. They received land grants and farmed on Upper Matecumbe. The Russells arrived first, followed by the Pinders and the Parkers. These three families acquired the entire island for about $20, the cost of recording their land grants!

The settlers cleared the jungles, fought mosquitoes, raised pineapples, limes, melons and vegetables, and fought more mosquitoes. Adolphus and Cephus Pinder opened the first canning factory in the Keys to can pineapples. The site was just east of today's Cheeca Lodge. Plantation Key was named for its pineapple plantations.

Henry M. Flagler started his railroad to Key West in 1903. This was a tremendous undertaking, bridging channels, filling swamps, cutting through jungles. Work stopped several times when hurricanes washed the tracks and equipment into the sea.

Islamorada's first post office opened on June 1, 1908, with John Henry Russell as postmaster. The island's railroad station was located near where the post office is today.

Islamorada in 1935

The railroad ruined the pineapple business. Cuban produce could be loaded on train cars, taken to Havana, placed on the ferry to Key West, then by rail through the Keys to New York, all without being unloaded. The Cuban labor was so cheap the Keys farmers could not compete. The late 1920's saw the Keys road opened. You could drive to the west end of Lower Matecumbe, take the ferry to No Name Key and then drive to Key West providing there was no exceptional high tide. The Labor Day storm of Sept. 2,1935, destroyed the railway and almost everything in the Islamorada area.

Water was piped into the area from the mainland in 1942. Electricity came officially in 1943. In fact, Islamorada had electric power several years before when Alonzo Cothron installed a diesel generator and a mile of lines to furnish power to a dozen homes and businesses. These amenities were responsible for many developments.

Since hurricane Donna on Sept. 9. 1960, the islands have blossomed with new marinas, motels, restaurants, apartments, dive shops and homes. Skiffs and small boats have been replaced by larger power boats and yachts. Small cottages which were built in the 40's and 50's have been replaced or added on to.

The homes of today are large modern ones whose owners spend at least several months in this tropical retreat. Permanent residents and visitors include in their number many famous people. George Bush, while president, visited Islamorada several times.