In 1885 three young adventurers left their Kentucky homes to seek fortunes in Florida. At the time, Florida was a popular destination for settlers who were anxious to try to make their fortunes in growing citrus. Land was cheap and plentiful, and the prospect of owning your own citrus plantation was a great allure. The three men, Andrew Walton Garnett, James L. Porter, and James Edward Hamilton, left Cadiz, Kentucky, in high spirits.

They first made their way to Bartow, Florida, but found the winter temperatures there still too cold for them. In short order, they moved on to Hypoluxo, Florida, ten miles south of West Palm Beach. Here they bought adjoining six-acre tracts for $200 each. Within no time the three men built a small house with a palmetto-thatched roof and set about the task of becoming citrus growers. Unfortunately, they soon realized that it takes a good deal of time for trees to mature and bear fruit. With plenty of time on their hands, they set out to find other ways of financial support. Before long, with a constant influx of new settlers, the community grew large enough for its own post office. Andrew Garnett saw an opportunity to earn some extra money, while waiting to harvest his first crop, so he took the job of local postmaster.

With the new post office now open, the mail route from Jupiter to Miami was split. Ed Hamilton placed a bid and won the contract for the southern portion of the route, from Hypoluxo to Miami. It paid $600 per year and was just the job he needed to help make ends meet while his citrus grove matured. Little did he realize that becoming a “barefoot mailman” would assure him a place in Florida history. In the late 1880s southern Florida was still very much a wilderness. There were few people, only a handful of towns, and virtually no roads. Nonetheless, the area was growing rapidly and getting regular mail was one of the more important aspects of starting and maintaining a community.

Regular mail meant on-going and reliable contact with the rest of the world. Prior to the implementation of “barefoot mailmen” carriers, the only alternative was to send mail by boat. It could take anywhere between three months to a year to get a letter to its final destination. The “barefoot mailman” arrived once a week, every week of the year. It took six full days for the carrier to make a round trip from Hypoluxo to Miami. A man in good physical condition, as Ed Hamilton certainly was, could make the trip with ease. Nights could be spent at either of two houses of refuge that had been built along the shore for shipwrecked sailors. Florida’s barefoot mailmen sacrificed much to deliver the mail. The two shelters on Ed’s route were located at Orange Grove (Delray Beach) and New River (Fort Lauderdale). It was not uncommon for him to stop at the Orange Grove house on his way south, arriving just in time to have supper with keeper, Charles Andrews, and his wife. Most likely, he would stop on the way back as well.

The long walk down the beach wasn’t always easy, but the mail had to get through, regardless of the weather conditions. Ed endured endless days of blistering heat, driving rains, and high winds. Hurricanes and squalls were not uncommon. Still the mail was generally reliable and arrived in good order. The mailman had to walk the route, because there was no way to provide enough water for a horse. Fresh water was scarce along the beach, and there were no roads or trails along the shoreline. In addition to his own drinking water, he had to carry everything he would need for the trip, plus the mail. He carried it all in a black oilcloth knapsack strapped securely to his back. If all went well, Ed could make the six-day round-trip and have a relaxing day off, working in his citrus grove before he had to start back again.

For a while, things went just fine. Ed made many trips to Miami and back without incident. Then on October 10, 1887, a Monday, Ed Hamilton left on what would be his final trip. No one knows what really happened to Ed, since there were no eyewitnesses to his death, but we do know that he visited with the Andrews family at Orange Grove on the first leg of his trip south. He stayed overnight and continued the following morning. When he didn’t return by Friday (which would have been the routine), Steven Andrews become worried. When he still had not arrived at the house of refuge by Saturday, Andrews set out southward in search of him. At Hillsboro Inlet 25 miles south of Orange Grove Andrews found Ed’s knapsack, mail pouch, and personal belongings, but there was no sign of Ed. The boat that mailmen used to cross the inlet was tethered on the other side in plain view. It appeared that an unknown person had borrowed the boat, rowed across to the far side of the inlet, and then continued south on down the beach.

A Florida state history marker, located at Boca Raton on the grounds of the Spanish River State Park, honors “barefoot mailmen” and Kentuckian James Ed Hamilton. The marker tells of Hamilton’s service and mysterious death, believed to have occurred while while trying to swim cross the Hillsboro Inlet. When Ed arrived, his mail-boat must have been on the wrong side of the inlet. It appears likely that he then attempted to swim across the inlet to retrieve the boat. Most people believe that Ed Hamilton died in his attempt to swim the Hillsboro Inlet. The weather had been bad for several days and the waters were especially rough and choppy. It would have been a dangerous swim, even for someone as young and strong as Ed. There was even some speculation by locals that he had been attacked and eaten by a shark or alligator. But no one really knows for sure. No trace of Ed’s body was ever found.

In 1892 a rock road was completed between Jupiter and Miami, and the Bay Biscayne Stage Line took over the job of carrying the mail. Today there is a modern concrete and steel bridge across Hillsboro Inlet. At the lighthouse, just north of the bridge on the east side of the road, is a plaque that tells of a brave young Kentuckian who came to Florida to seek his fortune in citrus, but instead became a legend. Ed Hamilton of Cadiz, Kentucky, became the lasting symbol of Florida’s legendary “Barefoot Mailman.”