Why go
The story makes a street walk more legible. John Simonton bought the island, while John Whitehead, Pardon C. Greene and John Fleeming held stakes in its early development. Their names entered the 1829 town plan. The contrast between investors who stayed briefly and Greene, who settled here, explains how a speculative purchase became a working town.
The full story
Soon after buying Key West, John Simonton divided the island into plots and sold shares to other investors. John Whitehead had first drawn his attention to its harbor. Pardon C. Greene settled on the island, built a business and served in local government, while Whitehead and John Fleeming spent much less of their lives here. Simonton moved between Key West and Washington, pressing for development and a naval presence. In 1829, William Adee Whitehead laid out the early town plan. Streets named for the principal investors still give Old Town part of its map. Duval Street honors Florida's first territorial governor instead. These names can turn a walk through the historic center into a way of reading the town's origins: land speculation, trade and the harbor all shaped the grid before Key West became the familiar destination of today.
Useful to know
- Notice the names on Old Town street signs as you walk between the harbor and Duval Street.