The original Native Americans themselves were extinct in the Keys by 1763, emigrating to Cuba as the English came into Florida. By then they'd become allies of the Spanish and helped them salvage their ship wrecks and learn to fish the waters. The "allies" part, however, only came later since Native Americans in the 1500s would typically kill or enslave any Spanish citizen or soldier unfortunate enough to be ship wrecked on the Keys reef.
After the original Native American tribes (the Calusa and Tequesta) left, there was a period of time where the Keys were uninhabited for the first time in a thousand years. Then in the 1800s another tribe arrived, the Seminole Indians who were being displaced by American settlers moving into Florida from the north. This tribe had a rocky start with early Keys settlers as the U.S. Army hunted them there and in the swamps of the Everglades where they hid. In 1840s the Seminoles staged a successful attack on Indian Key killing several of the inhabitants. The threat of Native American Indian attack was so great the remaining farmers and fisherman throughout the Keys fled to Key West until the conflict was settled. Today there are still Seminoles in the Keys, but they're friendly and come by truck or car from other parts of Florida to fish and enjoy the beautiful waters.
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In 1909 two brothers, Charles and George Chase, namesakes of the railroad’s nearby Chase Station, bought land on Sugarloaf and proceeded to pioneer efforts to grow sponges in the Keys, beginning in Sugarloaf Sound. The community of Chase was born, complete with a post office, housing and commercial buildings but the sponging venture failed and the town disappeared after the First World War. The name Sugarloaf likely came from a variety of pineapple once grown in the Keys, the “Sugarloaf”, or a nearby Indian mound resembling an old-fashioned loaf of sugar.
The Saddlebunch Keys, just west of Sugarloaf, are comprised of mostly mangroves and then there are small, uninhabited islands both north and south of the Highway until one arrives on Big Coppitt Key. The name Coppitt is said to be a derivation of the Old English word coppice, meaning “thicket.” Geiger Key is south of Big Coppitt at the southeastern corner of Boca Chica. An early Keys settler, Henry Geiger, obtained the land under the Armed Occupation Act of 1842, which was as an incentive to populate Florida if one met certain conditions to settle and remain on land for specified amounts of time to gain title, “Armed” because Indians were still a big threat to settlers.
Boca Chica is Spanish for “small mouth,” which may have referred to the narrow channel on the island’s western side now adjacent to Naval Air Station Key West (NAS Key West). Boca Chica is mostly salt marsh and mangroves but it’s home to a state-of-the-art training facility for air-to-air combat aircraft of all military services. Driving through the Keys one can often spot jet aircraft overhead and I’ve marveled at seeing some climb vertically into the sky.
Stock Island is the last island stop before entering Key West. The name comes predictably from herds of livestock that were once corralled there. Much of the island was altered by railroad crews recruited from adjacent Key West when jobs were scarce. They used the combination of “men, mules, dynamite and wheelbarrows” to prepare the land with fill and build up the roadbed for the coming railroad. The work was completed in 1907 with 200 men whose goal was to “complete 50 feet of fill per day” in preparation for the arrival of Flagler’s train in 1912. Stock Island was home to the Keys pink shrimp fleet and now has several nice marinas. Many commercial fishing boats still operate from there along with please boats.