The north-south Dixie Highway, established in 1915, was one of the earliest in a cross-country network of roads that would form our interstate highway system. Chicagoans could pick it up at the foot of South Michigan Avenue and take it all the way to Miami Beach.Photo Credit: State Archives of Florida

This is a story of two trailblazers – and the roads they left behind for us.

Hubbard’s Trail (Crete, Illinois)

In 1818, a young fur trader named Gurdon Hubbard arrived in Chicago. He left a profound mark on the city.

At that time, he might legitimately have been called “most interesting man in the world.” He was a frontiersman, a meat packer, an insurance underwriter, a banker, a steamship magnate, a legislator, and a civic leader.

During his early days in the area, he traveled the trail from trading post to trading post between Fort Vincennes, Indiana, through Danville, Illinois, to Chicago. He was called “Swift Walker” by the Indians; he once famously covered 75 miles in one night.

Hubbard wore a path that became known as Hubbard’s Trail. In 1834, the trail officially became State Route 1. You can follow it all the way into Chicago, where we know it today as State Street.

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Gurdon Hubbard landed in Chicago at age 16 as a young fur trader. His life and career would cover many miles and many industries.Photo Credit: Chicago History Museum

Hubbard established trading posts between Fort Vincennes, on the Wabash River in Indiana, back through Danville, Illinois, to Chicago. He wore a path that would become State Route 1; it was the first official state highway of Illinois and ran all the way into Chicago, where it became State Street. Photo Credit: Public Domain

Dixie Highway (Crete, Illinois)

Automobile dealer Carl Fisher saw the opportunity to promote cross-country car travel before there were interstate highways. Photo Credit: State Archives of Florida

Although the demand for automobiles was rapidly increasing in 1915, the idea of taking a long-distance, cross-country trip in one’s personal auto was still unthinkable. But a visionary Indiana businessman named Carl Fisher saw the future, and literally helped pave the way for a century of auto travel to come.

Fisher – who was also a partner in the Indianapolis Speedway – helped create and promote first the east-west Lincoln Highway, and then the north-south Dixie Highway, a series of connecting roads that made it possible for Chicagoans to get in their shiny new Packards, Pierce-Arrows, and Hudsons on South Michigan Avenue and make their way all the way south to the exotic beaches of Miami Beach, Florida. His idea created a whole new era in auto travel and possibly even fostered a new breed of Chicagoan: the snowbird.

The Dixie Highway was a network of roads that connected Chicago to Florida. Photo Credit: Public Domain via WikiCommons

In Chicago, traces of the Dixie Highway and the Vincennes Trail can be found winding throughout the south suburbs and on the South Side. Photo Credit: Ridge Historical Society

The pot of gold at the end of the highway was Miami Beach, especially attractive to winter-weary Chicagoans. In the 1920s, it was considered an exotic destination.Photo Credit: State Archives of Florida