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We officially started our Chicago to Santa Monica trip on Route 66 today. While Route 66 did not originally start at Navy Pier, it is now the ceremonial starting point and since we stayed in Mom's condo last night, we started our Pier to Pier trip driving over to Navy Pier before we got on Route 66 at Michigan Avenue and Adams Street.
As we drove on Route 66 through Chicago, we stopped to take photos of a Chicago Route 66 Mural at Lu-Lu's.
We also stopped at what used to be Castle Car Wash. Near it was a North Lawndale Route 66 informational sign.
Our first planned stop was at a coffeeshop. Our planned coffeeshop was not open as expected and we ended up at a Starbucks (more because Dad needed a bathroom than coffee, but we got coffee, too). If we hadn't stopped there, though, we would of missed the nearby Route 66 "Eating on the Run" info sign about iconic food places on Ogden Ave including that across the street is the oldest White Castle still operating on Route 66.
After Starbucks, our next stop was the Countryside Route 66 Centennial Monument.
As we continued to our next planned long stop, we made quick stops at seven Route 66 community monuments. A second one in Bolingbrook we missed because an event was going on that appeared to make access too hard.
- Berwyn Route 66 Community Monument
- Countryside Route 66 Community Monument
- Burr Ridge Route 66 Community Monument
- Willowbrook Route 66 Community Monument
- Darien Route 66 Community Monument
- Bolingbrook Route 66 Community Monument
- White Fence Farm Route 66 Community Monument
- Romeoville Route 66 Community Monument
The Harvester Park community monument was also expected to be a quick stop, but we discovered it was part of an impressive Route 66 themed playground and spent probably half an hour there exploring and playing
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Our first planned long stop was the Isle a la Cache Museum, where we learned about the fur trade and found an unexpected National Park stamp for the I&M Canal.
On the way to our next museum stop, we visited the Lockport and Crest Hill Route 66 community monuments
Next we learned about Joliet history including Route 66 at the Joliet Area Historical Museum and Route 66 Welcome Center.
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We then walked over to the Illinois Rock & Roll Museum on Route 66. This museum is still being developed, but the exhibits they do have done are well done.
I had been wanting a Route 66 Root Beer for my Route 66 bottle collection. I got one at the Illinois Rock & Roll Museum on Route 66 and after I started drinking it realized it honors the 100 years of Route 66 on the neck.
As we were ahead of schedule, we next headed to Martin & Emma Planinsek Grocery and Meat Market Museum, which was on my list to do only if we had time.
Next we stopped at Dick’s Towing Service and stood on some original Route 66 bricks.
We then headed across the street to the Joliet Route 66 Park. We walked around the park and read the various signs about Joliet, although only skimmed as already learned most of the info at the museum. There are some good sculptures and a large Route 66 sign in the park and a Joliet Route 66 Community Monument
While at the park, we also got ice cream from Rich & Creamy.
We then headed back to downtown Joliet to find the other Joliet Route 66 Community Monument (e ended up only driving by and not taking photos since we already took photos at the Joliet ones in the park and the history museums and there was not obvious easy parking nearby). As I had read about the Lincoln Highway and Route 66 crossing each other in Joliet, we also decided to check that out before continuing on to our next planned stop.
While parked near where the Lincoln Highway and Route 66 cross, we also walked over to take some photos of the Rialto Theatre.
Near the theatre, we also found a cool Route 66 themed bench. We learned about the benches from a billboard going into Lockport, which has 23, but we decided to not purposely try to find any as at the time we were behind schedule due to enjoying Harvester Park and did not want to end up rushing at the museums.
We then visited Lambert 1957 gas station, which is the oldest continuously operating gas station on Route 66. Pretty much just a typical modern gas station, but inside they do have photos and history of the gas station along with some Standard Oil and Amoco memorabilia.
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Our last stop of the day was to play a round of mini golf at Haunted Trails on Route 66 in Joliet.
See full list of Our Route 66 Adventures here and Google map here.

























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