At the westernmost point of Santa Rosa Island, along the shimmering sands of the Gulf of Mexico, the Florida Trail comes to an end at one of the most important historic sites in Florida’s Panhandle—Fort Pickens. Construction of Fort Pickens began in 1829 under supervision of the Army Corps of Engineers. President Abraham Lincoln considered Fort Pickens an important coastal defense, enough that he risked starting a war by sending Federal troops to occupy it. On November 22, 1861, the troops shot more than 5,000 cannonballs from Fort Pickens into Pensacola, its shipyard, and other fortresses on the western shore of the bay, convincing Confederate leaders to retreat and burn the city.

This segment of the Florida Trail is not an easy one. It’s out in the open, wind blasted and sun-drenched, and forces you to hike out and back (hurricanes wiped out the park road) or hire a water taxi to return you to Pensacola. But the sense of completion, and the weight of history, make this a compelling walk.

Guidebooks
The Florida Trail: The Official Hiking Guide
Along the Florida Trail