As the legend goes, deep in the swamps of Esto is the home of a demon-possessed, red-eyed alligator monster that made his way down from Alabama more than 100 years ago. Known as the “Loch Ness Monster” of Northwest Florida, Two-Toe Tom gained his name when he caught one foot in a monstrous steel bear trap and escaped with only two toes. The monster is said to inhabit nearby Sand Hammock Lake at the end Wiggler Lane, as well as other lakes and swamps in the vicinity. The monster is said to be more than 20-feet-long and has a reputation for attacking both livestock and humans. He was first described in Carl Carmer’s 1934 travelogue, “Stars Fell on Alabama.” Esto celebrates his legend each year with its Two-Toe Tom Festival, and sightings of him continue to this day.

From the park at Esto, return down 2nd Street North to State Road 79 and turn left. Follow State Road 79 south for 1.6 miles and turn right on State Road 2. Then drive west for 5.9 miles and turn left onto County Road 177 and immediately pull over for the next stop. Here is the Daniel Boone Trail.

State Road 2 follows the approximate route of the historic Pensacola – St. Augustine Road. This narrow horse path was the first major “superhighway” connecting the old East Florida capital of St. Augustine with the West Florida capital of Pensacola. It likely dates to the first Spanish era and is one of the true “Old Spanish Trails” in Florida. The road was first mapped by the British in 1778. They had gained control of Florida following the end of the French & Indian War in 1763. The famed American explorer and frontiersman Daniel Boone came to explore the newly acquired lands in 1765, leading a small expedition of friends and associates on a long walk across Florida. Back then, The Pensacola – St. Augustine Road was the only major trail from one side of the region to the other, and it is believed that Boone and his party followed the path. They likely passed nearby in 1765.

Esto is rich in history, but also in Lottery sales. The small town is ranked in the Top Ten of the “winningest” locations. The Friendly Mini Market at 1080 North U.S. Highway 75 falls in Florida’s Top Ten for both gross sales and winning ticket sales. Store Owner Jose Martinez says, “It’s the lucky store.”