American history is relatively young. But even in the U.S., we tend to think of “pioneers” as belonging to the seventeenth, eighteenth and nineteenth centuries. However, pioneers were eking out a living in Florida as late as the twentieth century. For example, it wasn’t until 1892 that there was regular mail delivery in southwest Florida to the new post office in Comfort, soon renamed Chokoloskee, more than fifty miles to the south of Fort Myers and another fifty miles on to Key West.
C.S. “Ted” Smallwood became Post Master on Chocoloskee in 1906. He remained Post Master until retiring in 1941 when his daughter took over until 1973.
What made them “pioneers” was that it was hard to get there from here no matter where “here” was. One traveled by boat through mosquito and alligator infested waters.
You might call Chocoloskee a typical Florida real estate development. The developers took an oyster bar and made an island out of it. But in this case, the developers were the First Americans, and it was about two thousand years ago. Passing fishermen from the First American Glades Culture dumped shells from shellfish on the reef which gradually rose from the water. Sand filled in. Mangroves took root. Very gradually the original oyster collection became an island.
Calusa people moved in and added shells deliberately building mounds. At twenty feet above the water, it was the highest land in the area. They established villages, fished and traded with others along the Gulf coast.
The Spanish came. Disease and war wiped out the Calusa. Seminoles, related to Cherokees and Creeks, moved to the island in the early 1800s along with occasional Caucasian hunters, wanderers, refugees and outlaws.
Modern settlement began in 1874. There were five families on the island when Ted Smallwood arrived in 1897 to open a store. He had his post office, store and trading post at his home on higher ground about a hundred yards inland but moved it to the water in 1917 for easier access to his settler and Seminole customers arriving by dugout and other boats.
Seminoles often traded hides, pelts and plumes. Not cured, they hung from ropes in the store until dried after which they could be sent to Key West and on to New York. Smallwood kept the Seminole’s cash safe in a box in his store.
The island wasn’t wired for electricity until 1955. Until then, kerosene was the principal fuel for everything from lanterns and cookstoves to heaters and refrigerators. Smallwood got a generator in 1945.
They blew a conch shell horn to tell island families the mail boat had arrived.
No conch was blown, but in 2017 Ray and Alie arrived in a car from Everglades City south of Naples. We drove over a bridge. The first bridge to the island was built in 1956.
American history is a young history.
The Smallwood Store is now a non-profit museum.
Click on photos to enlarge.