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Chokoloskee: Florida’s Ultimate Island Escape

Life on Chokoloskee, an island in the 10,000-Islands area of the Everglades in the Gulf of Mexico, radiates from Smallwood’s Store. It’s been this way for the past century since Ted Smallwood became the first white man to trade with the local Native Americans. The Smallwood family still runs the store, but it operates today as a museum and depository of all things Chokoloskee.


 

Planning a visit? Consult Okeechobee Co. Tourism.


That story began a couple of thousand years ago with pre-Columbian peoples known by archeologists as the Glades culture. During their habitation, mounds of discarded shells grew as high as 20 feet, making Chokoloskee far higher than the neighboring islands and nearby mainland. American settlement, never great, began in the 1870s and the remote 10,000 Islands country gained notoriety as a refuge for scoundrels escaping one scrape or another. The locals still tell the tale of the murderous Edgar Watson, who showed up after being tried and acquitted for the ambush killing of the Western outlaw Belle Starr. Watson met his end at Smallwood’s Store in 1910 in a confrontation with the islanders.

Chokoloskee is quieter these days for the 400 or so residents. A causeway was built in 1956 to connect the island to the mainland which makes it easier for visitors to charter fishing boats and eco-tours of the surrounding mangrove islands from “Florida’s Last Frontier.” Services must still be obtained in Everglades City at the northern terminus of the causeway, but islanders no longer have to listen for the blowing of a conch shell to pick up their mail from the delivery boat.

On Chokoloskee Island, isolated does not mean remote. The Tamiami Trail rolls just past the causeway, providing easy access to the cosmopolitan flavor of Naples and Marco Island. Chokoloskee is also one of the closest entry points to Fakahatchee Strand Preserve State Park, Florida’s largest state park that answers to the nickname of “The Amazon of North America.” In Everglades National Park, open-air tram rides touring the “River of Grass” can be boarded at the Shark Valley Visitor’s Center.

And back at Smallwood’s Store, perched on stilts over the Gulf of Mexico, the inventory contains 90 percent of the original goods when the cash registers stopped ringing in 1982. The only thing Ted Smallwood would not have recognized were the prices. And if you ask about a dark red stain on the wall, you will hear the story of Edgar Watson.

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