Chokoloskee is an unincorporated community and census-designated place (CDP) located at the edge of the Ten Thousand Islands in Collier County, Florida, United States.

Chokoloskee was inhabited by Native Americans for at least 1500 years before European explorers first recorded visiting the island.

It was briefly visited by Seminoles and the United States Army in the 1800s, and the current settlement can be traced back to 1874.

According to the United States Census Bureau, the CDP has a total area of 0.23 square miles (0.6 km2), all land.

Chokoloskee Island is an exception, as it reaches a high point of 20 feet (6.1 m) above sea level.

Chokoloskee Island was inhabited by the indigenous Calusa and their ancestors for more than 1,500 years before European explorers reached the area.

During the first three-quarters of the 19th century, Chokoloskee Island may have been occasionally visited by Seminoles, white hunters, "Spanish Indian" fishermen from Cuba and various "refugees from justice".

From there, an expedition of 75 men went up the Turner River, where they burned a Seminole settlement and a couple of planted fields.

These early residents farmed, fished and caught turtles, selling any surpluses in Key West.

After the highway reached Everglades City, it came by boat from there until the causeway to Chokoloskee Island was completed in 1956.

However, access to the outside world was still by boat to Key West or Fort Myers until the Tamiami Trail was completed and connected to Everglades City in the late 1920s.

"[15] Starting in 1896 Ted Smallwood carried the mail by sailboat between Chokoloskee and Marco Island via Everglades [City].

The Ten Thousand Islands country, including Chokoloskee, had a reputation as being a refuge for outlaws.

Edgar Watson, a native of Ridge Springs, in the Saluda Division of Edgefield District, South Carolina, showed up in the Chokoloskee Bay country in the early 1880s.

After that Ed Watson moved to the Ten Thousand Islands area, then part of Monroe County, where he bought a claim on the Chatham Bend River and began raising vegetables.

[20] Watson returned to the Chatham Bend area and began making syrup from sugar cane.

[21] Soon Watson had several people living at his place, including a man named Dutchy Melvin, who is said to have "killed a policeman[22] and burned a factory or two."

[23] Hannah Smith's body was later found in the Chatham Bend River by some settlers and given a burial.

Watson then bought some shells at Ted Smallwood's store and said he was going back to his place to kill Cox.

When Watson returned to Chokoloskee a few days later a crowd met him at the landing and, after a brief standoff, killed him.

[27] Matthiessen inspired the Decemberists to retell the story as "E. Watson" on their EP Long Live the King.

[28] Florida based swamp rock & blues band MOFRO relates some of the story in a song titled "Ten Thousand Islands" from the album Lochloosa.

He was registered with the State Board of Health as a midwife, treated injuries and illnesses, and extracted teeth.