The last two Route 66 begin signs we walked to were the ones on Adams St.
On the north side of Adams St a little west of Michigan Ave, is the classic brown Historic Route 66 begin sign.
In a park on the southeast corner or Adams St and Wabash Ave, there is another colorful Historic Route 66 Begins sign. Unfortunately, this one has ended up with a lot of sticker vandalism like the Start of the Trail sign.
See full list of Our Route 66 Adventures here and Google map here.
Destination Info:
Adams St just West of Michigan Ave (brown Historic Route 66 Begin Sign)
Adams St & Wabash Ave (colorful Historic Route 66 Begin Sign)
On Michigan Avenue near Adams St, there is a Route 66 Start of the Trail Sign. Instead of trying to take photos of the sign when we start our trip on Route 66, I walked over to them so we could really see them and take photos.
Sadly, the side facing the sidewalk has stickers on it, although not as bad as the sign on Adams and Wabash. The side facing the street is then hard to take a photo with because it is close to the street.
See full list of Our Route 66 Adventures here and Google map here.
Seeing the sign on Navy Pier was not on my original plan for our fall trip of Route 66 because it did not exist when I was making the schedule last summer. Of course, I had since added it to the schedule. However, I also keep finding other new things to add, so when I ended up with a few unexpected days in Chicago, I decided to go check out the different Route 66 begin/start signs and check them off our to do list now.
The Road Starts Here sign at Navy Pier is rather misleading in that Route 66 never went to Navy Pier, but it also never went to Santa Monica Pier where the End of the Trail sign has been for years.
Mom and I walked over and found the sign on our way to get some pizza for dinner at Navy Pier.
Inside Navy Pier there is a Route 66 themed souvenir kiosk, but I found it disappointing because it was pretty much just generic Route 66 things. Actually, overall I found the Chicago souvenir stores disappointing in that most of the Route 66 things were generic and not specific to Chicago or even Illinois. I could not find any Chicago Route 66 themed postcards at the Navy Pier shop or the two places we looked at on Michigan Avenue. I did finally manage to find some Illinois themed Route 66 postcards at a souvenir store on Illinois St.
Above is from when Mom and Dad walked over to check out the sign shortly after it was revealed in March.
See full list of Our Route 66 Adventures here and Google map here.
As we ended up with an unscheduled few days in Chicago, I took the opportunity to go find the different Route 66 signs in Chicago and check it off my list of Route 66 things to do.
On June 26, Mom and I walked over to Navy Pier to see the newest start sign to make it a pier to pier route from Navy Pier to Santa Monica Pier.
On June 27, Mom and I walked over to Adams and Michigan Avenue to the various begin/start signs in that area.
On our walk we also got some coffee at Fairgrounds Coffee on Michigan Avenue.
See full list of Our Route 66 Adventures here and Google map here.
On our way home from the Route 66 Centennial Kick Off in Springfield, MO, we didn't originally plan to do any Route 66 things, but we ended up going home via Michigan and decided to get off the interstate to at least eat an early lunch at Cozy Dog Drive IL. We ended up also driving a bit of Route 66 through Springfield, IL and visited the Lincoln Home National Historic Site.
Cozy Dog Drive In is the home of the original hot dog on a stick, which they call a Cozy Dog.
I had Cheese on a Stick.
I also had a Road Side Route 66 Root Beer.
See full list of Our Route 66 Adventures here and Google map here.
Stopping at Wally's was a last minute decision. I had heard about it and did not put it on our Route 66 plan for the fall mainly because it is a little bit off of Route 66 and I already have a lot of things on our schedule for when we are going through Pontiac. Thus, when we saw it as we were traveling the Interstate through this time, I decided we should stop.
Wally's is a lot like a Buc-ee's, although it did not seem to have quite as much variety of things and was not anywhere as crazy as most Buc-ee's locations are.
From the fresh popcorn area, I got the Flavor of the Week, which was Street Corn.
We also found some good Route 66 souvenirs here including a pair of pajama pants for Mik and a Centennial Route 66 Cola for my Route 66 bottle collection.
See full list of Our Route 66 Adventures here and Google map here.
While doing Route 66 we mostly plan to avoid the I-55, but when we were heading from Springfield, MO, to Indiana, we stuck to the fastest route other than doing some Route 66 in Springfield, IL. We stopped at the first rest area in Illinois (Homestead Rest Area) because we had heard there was an Illinois Route 66 passport and thought maybe we would find it here since it is also a Welcome Center.
The Welcome Center part wasn't open, but we did grab some of the Route 66 information they had available and found some Route 66 murals on the walls.
See full list of Our Route 66 Adventures here and Google map here.
The Gillioz Theatre does a free Sunday movie once a month. The May 2026 movie was Disney Pixar's Cars in honor of the Route 66 Centennial and the movie's 20th anniversary.
We got our free tickets when the box office opened at noon and then went to Big Whiskey's nearby to get some food while we waited for the doors to open.
The free movie also included a free bottled soda and a box of popcorn. There was also leftover boxes of popcorn you could grab on the way out and goodie bags that had little racing flags and Cars activty sheets.
Seeing Cars in a theater that has been on Route 66 for nearly 100 years was a fun activity to finish our weekend exploring Route 66 in Springfield, Missouri.
See full list of Our Route 66 Adventures here and Google map here.
Over the course of several days while exploring Route 66 in Springfield, Missouri, we did the Springfield 66: Sculpture Series Route digital passport to find all 16 of the statues. Once you check into enough of the statues, you can redeem for one of three pins. We ended up getting all the pins by the end of our visit.
Weathered But Not Forgotten
Into the Sunset
Preserving the Passion
Night Riders of the Mother Road
The Frisco
The Frisco
Wings of Route 66
The Buzz of the Mother Road
The Cardinal Spirit
Intersecting Journeys
Hope the High Road
Quiet Currents & City Lights
Quiet Currents & City Lights
Rerouted: From Mother Road to Motherboard
Welcome to Springfield
Game On, Springfield
Pasture Raised on the Mother Road
Pasture Raised on the Mother Road
Springfield 66: Sculpture Series Route pins
See full list of Our Route 66 Adventures here and Google map here.
In honor of Route 66's Centennial and the United State's 250th, Springfield, Missouri, added some rumble strips on the edge of Saint Louis St a little bit past the Queen's Gate 66 sculpture.
If you drive it at a steady 30 MPH, it plays "America the Beautiful." It took Dad a few tries to stay on it for almost the whole part as the last part is not lined up straight with the rest.
See full list of Our Route 66 Adventures here and Google map here.
The Route 66 Centennial Traveling Exhibit has a Missouri and New Mexico version on display in their respective states at various locations this year. We saw it while it was on display at the Gillioz Theatre in Springfield.
The exhibit features info about Route 66 including sites to see and its history in Missouri.
The exhibit also gave us a chance to see inside the Gillioz Theatre, which is also celebrating its centennial this year. A few days later we saw Disney Pixar's Cars here.
See full list of Our Route 66 Adventures here and Google map here.
