"Ted" Smallwood came to Chokoloskee Island as a permanent settler in 1897 and became postmaster in 1906, operating the post office from his home.

In 1917, Smallwood built the general store that also served as post office for the residents of Chokoloskee Island.

[2] The Smallwood Store was featured as one of the haunted locations on the paranormal TV series Most Terrifying Places in America in an episode titled "Restless Dead", which aired on the Travel Channel in 2018.

[3] The episode told the story of "Bloody" Ed Watson, an outlaw who allegedly fled Oklahoma after killing a member of Butch and Sundance's Hole-in-the-Wall Gang and wound up in the Everglades.

But when they wanted to move on, Watson would take them to the Smallwood Store so they could catch a boat to Fort Myers or Key West.