Chokoloskee – Big History, Little Island

The Little Island With a BIG History

Chokoloskee, Florida

There is a little island at the end of a road in the Everglades that has more historical significance than some major cities! Chokoloskee, Florida is a ¼-mile square patch of land bordering the Everglades to the north and east, and the Ten Thousand Islands on the west and south. Most of the island is slightly above sea level due to the mounds of shells from hundreds of years of Indian occupation.

Today, the 400 or so inhabitants are involved in the fishing business. Some as charter captains, others as commercial fishermen and many more run various support businesses like motels, small resorts and campgrounds. Basically, you could say this is the classic definition of a sleepy little fishing village.

Beginning in the late 1800s, the Indians were gone, killed or forced out, and settlers took their place. The area was fertile and full of fish and oysters. On the mainland were deer, various birds, raccoons and other meat sources. Chokoloskee became a trading center of some repute. Locally grown tomatoes, cane syrup and fish were traded for needed supplies. Regular boats traveled between Chokoloskee and Key West. Most news from the outside world came from the sailors on board these vessels.

History has another view of Chokoloskee and the surrounding bay – and it’s not so sleepy! The area was extremely remote. The causeway existing today wasn’t built until 1956. You could only reach the island by water, which was perfect for some notorious individuals avoiding the law. There are numerous books written about various Everglades outlaws, none more documented than Edgar J. Watson. Watson was an alleged serial killer. He even shot Belle Starr, the one-time girlfriend of Jesse James and/or Cole Younger during their outlaw days. Watson was never convicted, despite evidence to the contrary. He lived along the banks of Chokoloskee Bay by farming. Legend has it that his farm hands would disappear when it was time for payday. Bodies were never found, but there were a lot of fat alligators around.

Among the criminal mischief surrounding the area, nothing was more prolific than moonshine. It has been reported that few shipments of vegetables left the island without some “low bush lightning” being sheltered by stacks of vegetables. The moonshine would end up in Key West.  Prior to the end of prohibition, the swamps were filled with the smell of “shine”.

Notable scoundrels roaming the area were plume hunters. The price for feathers from birds in the area was about the same as gold! Hat makers in New York paid handsomely for the bright feathers of egrets, herons, ibises and spoonbills in the Everglades. By the early 1900s conservationists realized the bird populations were being decimated. However, it wasn’t until after several game wardens were shot trying to make arrests that the public outcry stopped the plume hunting.

Noting the importance of Chokoloskee as a trading area, Ted Smallwood opened a trading post in 1906 on the south end of the island. People from all around the area came for everything from basic food supplies, to mail and other goods from Key West. It was a common sight to see Seminole Indians, local fishermen, farmers and hunters congregating at the store in skiffs, dugout canoes small schooners and rowboats.

The Smallwood Store, after several hurricane remodels, still stands today as a museum and tribute to Ted Smallwood. Visit the store and museum most days from 10 AM to 5 PM. Like most things in this laid-back atmosphere, you may want to call to make sure they didn’t go fishing!

Chokoloskee is 4 miles south of Everglades City, at the end of Copeland Road. It’s difficult to get lost in this area of Florida – there are few roads! It should be noted the Chokoloskee Bay area has some of the best inshore fishing in the world. Redfish, snook, trout and many other species are available. Take some insect repellent fishing – the “Swamp Angels” are pretty heavy certain times of the year!

Smallwood store
Prior to the caueway, Ted Smallwood's Store was only accessible by water. Traders, farmers, indians, moonshiners and all visited by boat.
Don't bet on everything being open year round except for fishing.
Photo of Chokoloskee Island Park and Marina
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There is only one way on and off the island without a boat.
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Fishing is a way of life in this area. Exceptional inshore opportunities for snook, redfish, trout, sheepshead cobia and many more.
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The legend of Edgar J. Watson continues to grow over the years. They say the home below was on Chokoloskee Bay was where he disposed of his farm hands.

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