The route covers approximately 69 miles through Pasco and Hernando counties, crossing a region dominated by cattle ranches, farmland, small rural communities and scattered suburban developments that expanded during recent decades. The ride connects historic communities such as San Antonio, Saint Leo, Blanton, Brooksville, Spring Hill and Masaryktown, along with several ghost towns and protected areas near the Croom Wildlife Management Area.
The journey begins in San Antonio, a small town established during the 1880s as part of the massive land development operation promoted by Hamilton Disston after purchasing millions of acres in Florida. The area was promoted by Edmund Francis Dunne as a Catholic and German colony in west central Florida. The former Orange Belt Railway crossed the region, and several historic structures connected to that era still survive, including old schools and railroad-related streets.
Nearby lies Saint Leo, where German Benedictine monks established a monastery, abbey and eventually present-day Saint Leo University, one of the oldest Catholic institutions in Florida. The region still preserves a strong religious and agricultural heritage. Farther ahead the route crosses former railroad settlements such as Chipco and Blanton, communities that emerged along the Orange Belt Railway during the late nineteenth century and remain surrounded by ranchland, forests and open grazing areas.
The ride continues near vanished settlements such as Jessamine and passes through Rolling Acres, Hill ’N Dale and Spring Lake, small rural communities located among gently rolling hills uncommon in Florida. Near the route lies the extensive Croom Wildlife Management Area, one of the largest protected natural regions in west central Florida. The scenery alternates between pine forests, grasslands and low hills that contrast sharply with Florida’s stereotypically flat landscape.
Farther ahead the route reaches Brooksville, the seat of Hernando County and one of the most historically complex towns in inland Florida. The area developed around early pioneer settlements and military forts established during the Seminole Wars. The city still preserves historic buildings, old courthouses and traditional commercial streets. Brooksville also carries a long history marked by racial segregation, violence against African Americans and strong Ku Klux Klan influence throughout much of the nineteenth and twentieth centuries.
The route continues through Wiscon, Brookridge and High Point before entering Spring Hill, a massive suburban community developed during the real estate expansion of the late twentieth century. Spring Hill was built over environmentally sensitive land and now represents one of the fastest growing urban sectors in Hernando County. Farther ahead lies Shady Hills, known for pigeon racing, and later Masaryktown, founded in 1924 by Slovak and Czech immigrants who named the settlement after President Tomáš Garrigue Masaryk.
The final section returns to quieter rural landscapes through Garden Grove, Darby and Saint Joseph, another settlement originally promoted by Edmund Dunne during the nineteenth century. The route eventually returns to San Antonio after crossing secondary roads surrounded by ranches, forests and small agricultural communities that still preserve much of the atmosphere associated with old rural Florida.
