In 1926 new horseless carriages created a need for a network of roads for people to drive them on. Thus the federal highway system was launched with Route 66, dubbed The Mother Road or Will Rogers Highway, being the path west from Chicago to L.A. Folks were already heading west for land, jobs, and to find their fortune in one way or another.

Cathryn and I packed up the Impala and headed to Chicago on June 10th. We headed to Chicago, where Route 66 originates, and walked around downtown. A beer and a cheeseborger at the Billy Goat gave us the fuel to carry on and check out the Riverwalk. We had dinner and finished the night at Andy’s Jazz bar, a great send off from the windy city.

We stayed at the Congress Plaza, a beautiful turn-of-the-century hotel near the waterfront. Pete, the hotel security guard took us on a private tour showing us the first air-conditioned ballroom in the U..S. and a backroom where Al Capone hung out and played cards. Apparently him and Elliott Ness stayed in the same hotel at the same time, unknown to the Treasury Agent.

Breakfast was had at Lou Mitchell’s, another Chicago Landmark, a block west of where Route 66 officially starts. When the place gets busy they feed you Mild Duds or donut holes while you wait in line. I saw a group of Chicago PD task force cops who looked like Storm Troopers without the plastic suits.

Staying on old 66 took us out of downtown and into the burbs and eventually into Jolliet, home of Jake and Ellwood Blues and the famous Rialto Theatre. Illinois takes you back to the 50’s and 60’s by keeping old steel and neon signs from hotels and restaurants along the roadside. There are giant roosters and muffler men that are corny to say the least, but a odd collection of artifacts that coax you along as if you’re on a scavenger hunt.

Our second night found us in Springfield, near the State Capitol Building. Friendly security staff there allowed us to tour the building early in the morning before any of the politicians arrived for work. Staying on 66 takes you through many small towns that you can’t find on a regular map. The population of many have dwindled over time, especially when the Interstate system replaced the old U.S. highways.

More giant statues and Abe Lincoln on the world’s largest covered wagon line the road west. Lots of abandoned motels and gas stations remind you of a lost era. Even giant steel bridges have been left to rust, like the one that crosses the Mississippi into Missouri. We got off the road for a closer look but found access blocked because of the high water levels and flooding in the area.

Missouri offered more nostalgia on historic 66. We decided not to stop in St. Louis and carried on southwest seeing things like the world’s largest rocking chair and a group of 85 seniors on motorcycles that made me feel like a wimp for being in the car. We saw a replica of the Hubble Telescope and met a guy named George who ran an old Sinclair gas station in Paris Springs. Cathryn gave him an Ontario licence plate to add to his collection of memorabilia.

Acting on George’s info we found a great hotel overlooking a lake in Carthage. The stone courthouse there is one of the most photographed sites in the state, second to the arch in St Louis. George also gave us the name of a small town called Red Oak 2, where a local artist bought and relocated all sorts of buildings and mementos of his old town before they disappeared forever.

We got a true taste of southern hospitality while walking around Red Oak when an elderly man named Jim invited us onto his porch to set for a while. Jim was the former mayor of Carthage and a travelling salesman who covered 8 states! He did very well for himself and built a beautiful home in Red Oak – he offered us a tour to prove it to us before we left.

Route 66 continues southwest through the top corner of Kansas, but you’re in Oklahoma before you know it. That state is the worst for signage along the old road and it didn’t have as many sites. Some sections of the mother road are no longer in existence but the Interstate parallels its route and takes you on to the next part for exploration.

We spent Friday the 14th in Oklahoma City, a pleasant surprise for a big city. We stayed in the Bricktown area and were blown away by the landlocked canal lined with restaurants and bars and throngs of people. Windsor’s former Mayor was laughed at when he suggested doing something similar as a tourist draw.

The Blue Whale was probably the most odd site along the road and a couple of empty or ghost towns were well worth the drive through. Lots more abandoned gas stations and hotels and dozens of rusty old trucks and cars kept us watching both sides of the road. We got to cross the state line on a crusty old cement two lane section of road where the Texas road sign was plastered with all kinds of stickers. Amarillo was our home for the night and we found some delicious barbecue at a place called Rudy’s to end the day.

And so in six days we’ve covered half of the 2,450 miles from east to west. I wonder what lies ahead in the next two thousand or so miles?