The route covers approximately 77 miles through Duval and Nassau counties, crossing urban districts, historic railroad corridors and extensive forested landscapes in northeast Florida before once again reaching the Georgia border along the Saint Marys River. The ride connects Southwest Jacksonville, Northside Jacksonville, Nassau Village-Ratliff, Callahan, Hilliard and Boulogne while following much of the route once shaped by the historic railroads that fueled economic growth throughout the region during the nineteenth and early twentieth centuries.
The journey begins in Southwest Jacksonville, a vast urban district historically linked to the Florida Central and Peninsular Railroad. Former railroad communities such as Lavilla Junction, Marietta, White House and Clarks were gradually absorbed into Jacksonville’s urban expansion, though active freight rail lines operated by CSX, Norfolk Southern and the Florida East Coast Railway still dominate the landscape. The route crosses industrial districts, massive rail yards and suburban neighborhoods before reaching the northern sectors of the city.
The ride continues along the historic Kings Road, an eighteenth century route originally constructed by the British to connect Saint Augustine with Georgia. Along the corridor appear former railroad and agricultural settlements such as Pickett, Britzville and Dinsmore, now incorporated into Northside Jacksonville. Nearby survive natural areas such as the Thomas Creek Wildlife Management Area, where the scenery gradually changes into larger forests and pine woodlands.
After entering Nassau County the route reaches Nassau Village-Ratliff and later Callahan, one of northeast Florida’s principal historic railroad crossroads. Callahan emerged during the expansion of David Levy Yulee’s Florida Railroad and later became an important connection point for multiple railway companies. The area also witnessed the Battle of Alligator Bridge during the American Revolutionary War, when rebel forces unsuccessfully attempted to invade British East Florida.
Farther ahead the route follows former railroad stations such as Dyal and Hilliard. The latter began as a stagecoach stop before becoming a lumber and railroad center during the late nineteenth century. The landscape remains dominated by pine forests, rural properties and scattered communities such as Evergreen, Lessie and Andrews.
Eventually the ride reaches Boulogne, a historic border community near the Saint Marys River. During much of the twentieth century the town served as one of Florida’s main gateways for travelers entering from Georgia. The area once contained motels, orange juice stands and tourist centers promoting the Sunshine State. However, after the construction of Interstate 95 and the decline of traffic along the old highway, much of that infrastructure was abandoned.
The final section arrives at the bridge crossing the Saint Marys River, the natural boundary between Florida and Georgia. Nearby once stood vanished settlements such as Traders Hill, Orange Bluff and Woodstock. The region also preserves protected forests such as Ralph E. Simmons State Forest and historic sites including Kings Ferry, documented as early as the eighteenth century. From there the route returns toward Jacksonville through the same rural, railroad and forested landscapes that continue to define this part of northeast Florida.
