Sugarloaf Key: Nature, Trails and History

Two geographical details are useful for getting oriented on Sugarloaf Key. The Overseas Highway crosses Sugarloaf Key twice: at Upper Sugarloaf and at Lower Sugarloaf. The Florida Keys WEA stretches 80 miles from Key Largo to Sugarloaf and Saddlebunch Keys. Local place names thus meet the wider scale of a protected area that encompasses several Keys.

Nature and Landscape

The Florida Keys WEA contains some of the best remaining undisturbed tropical hardwood forests preserved in Florida. Nature-based recreational opportunities in the area include hiking, paddling, kayaking and sightseeing. At Sammy Creek Landing, restored native vegetation attracts numerous butterflies. This places a large natural area alongside a named location and its vegetation as distinct nature-related themes. The activities also have different emphases: the range extends from hiking on foot to paddling and kayaking on the water, with sightseeing adding to the options.

Trails and History

The Lower Sugarloaf/Saddlebunch Key “End of the Road” Trail follows the remains of old State Road 4A, the original road to Key West. Its connection to the former route gives the trail a specific historical context. The Florida Keys Overseas Heritage Trail is a multipurpose route for cyclists and pedestrians, as well as a recreational and alternative transportation corridor for the Florida Keys. The two trails have distinct functions: the “End of the Road” Trail focuses on the historic road, while the Overseas Heritage Trail serves multiple purposes for recreation and alternative transportation.

The Bat Tower on Sugarloaf Key was built in 1929 for Judge Clyde Perky. It was intended to attract and house bats, in the hope of alleviating the mosquito problem that was rampant in the Florida Keys at the time. On September 10, 2017, the tower fell during Hurricane Irma; the structure no longer exists. Its history therefore encompasses both its original purpose and the tower’s eventual end.

Around 1909, Mangrove Mama’s began as a railway post on Henry Flagler’s Overseas Railway. The building behind Mangrove Mama’s was once the home of the railway station agent and later served as a one-room schoolhouse. The sequence from the station agent’s home to a school shows a change in the building’s use and adds later everyday functions to the history of the railway post.

Recreation and Fishing

Sugarloaf Shark Park has a walking path with exercise equipment, fields for baseball, football and soccer, and a pavilion. The walking path and exercise equipment are situated alongside several field sports. This sets the park’s focus apart from the nature-based opportunities at the Florida Keys WEA and offers a concrete comparison for planning recreational activities.

A 2025 report describes the Sugarloaf Showdown as a catch-and-release fishing tournament targeting bonefish, permit and barracuda. Tournament rules may change.

Explore more destinations: Key Largo, Layton, Stock Island, Islamorada, Key West, Key Colony Beach, Marathon, Little Torch Key

For the broader travel overview: Monroe.