My move to the Florida Keys in 2001 was filled with unknowns. I was apprehensive, nervous even. I was coming to a strange new land. It was not the strange new land encountered by the island chain’s early pioneers, but challenging in terms of the circumstances of the day. I was attempting to forge a new path and start fresh, start over. By comparison, I do not think I would have had the determination or the fortitude to have been a pioneer and moved to these islands 150 years ago.
The early pioneer families arrived largely from the Bahamas. Because the arrival of Commodore David Porter and his West Indies Squadron in 1823 brought a sense of security to the island, a vast majority of the early settlers set sail for the ever-increasingly civilized outpost of Key West. Not only did the island offer a deep natural harbor, it was conveniently located along shipping routes connecting the Mississippi River to east coast markets.
By 1825, outlying communities had begun to blossom on Vaca and Indian keys. The Vaca Key community, known as Port Monroe, was located in what is today the Marathon area. Interestingly, it was one of Port Monroe’s founders who funded the development of a general store, not at his locale, but on Indian Key to the north. Of the two sites, Indian Key proved the more successful.
Located approximately one mile off the Matecumbe keys, the roughly 11-acre island is approximately midway along the Florida Reef. Though it did not host a military presence during the community’s early development, a naturally occurring deep harbor and a nearby source of freshwater made Indian Key a convenient home to wreckers and fishermen plying their trade along the reef line.
By 1829, Indian Key offered a hotel, restaurant, saloon, and game room including billiards and nine-bowling. It additionally offered the convenience of a general store. During the second escalation of the Seminole War, Indian attacks began moving steadily south circa 1836. As news of Indian aggressions spread through the island chain, most people began to abandon the Upper and Middle Keys for the safety offered by the military presence at Key West. When Indian Key was attacked August 7, 1840, six lives were lost.
In the years following the second escalation of the Seminole War, and through the third escalation (1855-1858), the Upper Keys remained largely uninhabited. A notable exception was the family of Richard and Mary Russell who left the Bahamas, bound for Key West, circa 1838. They would become one of the first pioneer families to arrive in the Upper Keys, settling on Upper Matecumbe circa 1854.
By 1870, 134 people were documented as living on the Upper Keys. Of those 134 people, roughly 92 percent were either natives of the Bahamas or children born to them. Though the Indian Key community had largely been destroyed by the 1840 Indian attack, as of 1870 46 people were documented as living on the island. By comparison, 13 people were counted on Upper Matecumbe, today the heart of Islamorada.
After the 1870 census, the population of the Upper Keys began to steadily increase. First, the viable industry of commercial pineapple farming had been established. Second, the Homestead Act passed by President Lincoln in 1862, allowing any U.S. citizen, or potential citizen, who was either over 21 years of age or the head of a household, be it man, woman, immigrant, or freed slave, the ability to claim up to 160 acres of undeveloped and unclaimed land from the public domain was about to become applicable to the Florida Keys. One of the caveats of the Homestead Act was that the lands had to have been surveyed which did not begin in the Keys until circa 1872.
Perhaps the earliest homestead claim in the Upper Keys was assigned to Richard and Mary Russell who settled on the northeast end of Upper Matecumbe Key. Richard and Sarah Pinder, who had been farming on Indian Key in 1870, would make the second homestead claim on Upper Matecumbe.
Because the market at Key West was not readily accessible to those settling along the Upper Keys, farming became a twist on the pioneer experience. Families grew gardens for their personal use, but also as a means of trade between neighbors. Some families also ventured into commercial farming which, in terms of the pineapple for instance, became a lucrative industry. Between the need for family farming, the clouds of mosquitoes, lack of running water and electricity, the early pioneers of the Florida Keys were cut from the kind of stock not often seen today. Several days without running water and electricity experienced in the wake of Hurricane Irma showed just how accustomed we have become to modern conveniences.
All of which makes any apprehension I may have felt when I dared to move to some strange new land seem silly. With Winn-Dixie just up the road, as well as convenient tavern to find a cold beer, my arrival in the Florida Keys was absolutely cushy by comparison.
Brad Bertelli is a freelance writer, Upper Keys historian and curator of the Keys History & Discovery Center. He has written or co-written six books about Keys history, snorkeling, and the Netflix series Bloodline. His column, Notes on Keys History, appears monthly in The Reporter. To learn more local history, visit the Discovery Center located on the grounds of The Islander Resort. Reach Brad with comments and questions at firstname.lastname@example.org.