EVERGLADES CITY and CHOKOLOSKEE, at the entrance to the Western Everglades, were two frontier outposts frontier outposts until 1923 when Barron Collier made Everglades City the seat of Collier County and supply depot for the construction of the Tamiami Trail. Prior to the boom, this isolated region was Florida's last outpost for fur trappers, plumage hunters, Cuban fishermen, and people with a disdain for modern civilization.


WHERE TO START: Everglades City can only be reached by BOAT or DRIVING SOUTH ON FL29, past the 1926 Everglades High School, pride of a town that has lost population since 1930. A. You'll notice houses on stilts and air boat rides along the river.

TURN RIGHT ON BROADWAY, past the Spanish-style railroad depot with its barrel tile roof and past the frame Community Church. You won't miss the OLD COLLIER COUNTY COURTHOUSE, a 1926 four-columned temple that seems totally atypical for a frontier village.

At Shorter Avenue is the (1) COMPANY LAUNDRY BUILDING (1928) and the (2) BANK OF EVERGLADES (1926).

Everglades Bank Now Hotel Everglades Museum

Everglades Rod & Gun Club Rod & Gun Rustic Florida

At 200 Riverside Drive by Broadway is the wonderful ROD AND GUN LODGE (1890), built by Collier to entertain friends, but expanded to serve tourists. Go inside and imagine Ernest Hemingway and Ted Williams have a drink at the bar after a serious day of bone-fishing in the Ten Thousand Islands. This is a unique place to stay or eat or rent a boat.

CONTINUE SOUTH ON FL29 to reach CHOKOLOSKEE ISLAND, but stop at the 80-foot E. J. HAMILTON OBSERVATION TOWER for a view of the 10,000 Islands or visit the EVERGLADES NATIONAL PARK HEADQUARTERS, which has boat tours in the Everglades' Western limits.


This area of Florida still has the feel of pioneer days, but please remember that between May and October, the tropical areas are the domain of mosquitoes and bugs.  CHOKOLOSKEE ISLAND is a 150-acre mound in a shallow inland sea. Follow the signs to the amazing (3) SMALLWOOD STORE (1917), a one-story board and batten trading post on pilings. Ted Smallwood once ought the entire island in 1896 and his structure was grocery, post office, and symbol of the end of the Florida West Coast.

Ted Smallwood

Smallwood Store

The rest of the island consists of fishing camps, mobile homes, and the remnants of Calusa mounds.