Where is Chokoloskee Florida – Historical Island in the Everglades

Where is Chokoloskee Located

Chokoloskee, Florida is located on a ¼-mile square island in Collier County, bordering the Everglades to the north and east, and the Ten Thousand Islands on the west and south.

Chokoloskee Island is 40 miles southeast of Naples, Florida in the heart of the Everglades.

Directions to Chokoloskee

While it may seem complicated, it is relatively easy to get to Chokoloskee, Florida. The easiest way is to find Everglades City and follow the directions to Chokoloskee.

Specifically, take Route 41, the Tamiami Trail, east from Naples. After traveling about 30 miles you will see Route 29 south to Everglades City. Take this road and as you come into Everglades City you will see the sign for Plantation Island and Chokoloskee Island. It will be called Smallwood Road.

The island is just over a small bridge from Everglades City – see the map of Chokoloskee Florida below.

Most of the island is slightly above sea level due to the mounds of shells from hundreds of years of Indian occupation.

Chokoloskee is in the middle of the Everglades. The most accessible part of the Everglades is surrounding Chokoloskee Bay.

Chokoloskee Florida History

Beginning in the late 1800s, the native 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 Florida became a trading center of some repute. Locally grown tomatoes, cane syrup and fish were traded for needed supplies.

Regular traveling trader boats traveled between the island 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! 

Chokoloskee Island Gets Contact with the Mainland

The causeway existing today wasn’t built until 1956. Prior to the bridge, 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 who lived on Chokoloskee Bay.

Watson was an alleged serial killer. He even was charged by locals saying he 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.