Upper Matecumbe Key has been inhabited periodically since about 2000 B.C. Long before European settlement of Florida, Native Americans lived there, and surviving Indian sites indicate that the earliest settlers depended primarily on marine resources for food while also hunting game and gathering fruit. After the Spanish entered in the sixteenth century, their numbers fell sharply because of disease, warfare, and migration, and by the latter part of the eighteenth century this native population had disappeared. When Henry M. Flagler's Florida East Coast Railway entered the Florida Keys in 1905, only a few families lived on Upper Matecumbe. The Russells, Pinders, Parkers, and a few others from the Bahamas had settled there in the 1800s and built a peaceful life despite isolation, harsh climate, and insects, collecting sponges, salvaging shipwrecks, fishing, and growing limes, pineapples, tomatoes, and melons for market. The waters provided fish, conch, lobster, and turtle, trigger fish skin was used for scrubbing, and people planted crops among porous rocks by placing lime seeds in pockets of leaf mold. In 1900, fewer than 100 people lived on Upper Matecumbe, while Key West had more than 17,000 citizens. Without roads or cars, residents walked the shoreline or sailed to school, church, and visits. In 1933 the Matecumbe Methodist Church on the beach where Cheeca Lodge stands today had 92 members, and all early buildings stood just above the high water mark. After the railroad came through Matecumbe, many local people of Bahamian heritage became fishing guides for northern visitors, and the Caribbee Colony fishing resort was established at the south end of Islamorada. The Labor Day Hurricane of 1935 killed countless family members and destroyed homes, the church, and the adjacent beach school, leaving only the cemetery as a reminder of the earlier life, but most survivors remained on the island. Islamorada was the name given to the first train station on Matecumbe Key by William J. Krome, who was in charge of constructing the Overseas Railroad, after a sailing vessel owned by Johnny Brush Pinder; in Spanish, Islamorada means "island home."