Starting Our  Route 66 Journey—In Segments

By Mark Anderson

It had been a long-standing dream of mine to drive Route 66 from its beginning in Chicago to its end in California, and in September of 2017 my wife Carolyn and I set out on that wonderful adventure from our home in Cortland, Illinois. However, we began our journey in “stages” prior to hitting the trail for the long haul.

Because we reside relatively close to Chicago, we found that it was simple to break the Illinois portion of the trip into three segments, picking up each time where we’d stopped on the previous drive. (Day 1-Chicago to Dwight; Day 2-Dwight to Bloomington-Normal; Day 3-Bloomington-Normal to Staunton.) We were accompanied by John Weiss’s New, Historic Route 66 of Illinois (8th Edition), an easy-to-follow guide which made each of our segments in Illinois interesting, fun, and on track.

By doing it this way, we could make a “day” out of each segment, enjoying—unhurriedly—the many places and historic spots along the old highway. And so when we were ready to get out on the Mother Road and drive it the rest of the way to Santa Monica in September, our starting point was in Staunton, a short distance to the Chain of Rocks Bridge and the Mississippi River.

I had been eager to visit the Chain of Rocks Bridge, having never done so before, and I was particularly interested in seeing the odd sharp turn it makes near the Missouri side. Unfortunately, because the access to the bridge was closed to access, we could only see the bridge from a distance as we crossed over the I-270 bridge, westbound to St. Louis and beyond. 

I was disappointed but knew that sometime down the road I’d be able to get to the Chain of Rocks Bridge, which we did in June of 2021, where we actually got to drive over and back on the bridge with our group, The Route 66 Association of Illinois, during its annual Motor Tour weekend.

Once we crossed the river, I had a feeling that our journey was now “officially” in play! So many miles and unfamiliar territory lay ahead. It was a wonderful feeling of freedom on the open road with so many little towns and nooks and crannies for us to see and enjoy on The Mother Road!