The Evolution of Route 66's Starting Point: Tracing the Origins of an American Icon

Updated August 19, 2023

As you embark on your own journey along Route 66, the question of where it truly begins may arise and it's not as clear cut as you might think! Let's dive into the fascinating history of the starting point of Route 66 and how it has evolved over time...

A Shifting Eastern Terminus

Assuming you're traveling westbound, Route 66's starting point is rooted in the vibrant city of Chicago, Illinois. However, the exact location of the eastern terminus has undergone shifts due to various factors, most notably the introduction of a one-way system on Jackson Blvd and Adams St in the 1950s.

The original inception of Route 66 in 1926 placed its starting point at the intersection of Jackson Blvd and Michigan Ave. This intersection marked the beginning of the great cross-country journey that captured the spirit of exploration and the promise of the open road.

Navigating the One-Way System

The mid-20th century brought changes to traffic flow in Chicago, resulting in the introduction of a one-way street system on Jackson Blvd and Adams St. This alteration necessitated adjustments to the route's starting point, and as a result, the iconic "Route 66 Begin" sign now stands at the junction of Adams St and Michigan Ave. This shift in location, while relatively small in distance, symbolizes the evolving nature of Route 66 and its ability to adapt to changing urban landscapes.

A Further Complication: 1937's Change

Adding another layer of complexity to the story, in 1937, the official eastern terminus of Route 66 underwent yet another change. This time, the starting point was moved to where Jackson Blvd meets Lake Shore Drive. This alteration was intended to improve the alignment of the highway and streamline its path through the city.

Options for the Modern Traveler

In the present day, for those embarking on the westward journey of Route 66, there are multiple options for where to officially start your road trip. You can choose to begin at the original 1926 starting point where Jackson Blvd meets Michigan Ave. This location pays homage to the earliest days of the highway and the adventurers who first set out on its path.

Alternatively, you can opt for the starting point that has been in place since 1937—where Jackson Blvd meets Lake Shore Drive. This choice reflects the adjustments made to Route 66 to enhance its efficiency and alignment over time.

For the thorough and enthusiastic explorers, the EZ66 Guide provides a unique opportunity. It outlines a loop that encompasses both starting points, allowing travelers to experience the entirety of Route 66's Chicago origins.


As you prepare to embark on your Route 66 adventure, the tale of its starting point serves as a reminder of the highway's rich history and the constant evolution of the landscapes it traverses. Whether you choose to begin your journey at the original 1926 site, the 1937 alignment, or both, each starting point holds a unique connection to the past and a promise of the experiences that lie ahead. So, whether you're drawn to the nostalgia of the early days or intrigued by the engineering refinements, the starting point of Route 66 offers a gateway to a cross-country expedition that captures the essence of the American road trip.

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