I did a stretch of Route 66 today, from Joliet, IL to Pontiac, IL.
In Joliet I toured the state prison, which is the prison that Jake is released from at the start of Blues Brothers. The prison operated from 1858 to 2002 and the tour is 90 minutes long and full of stories. The prisoners would play softball once a week against volunteer teams from the area, and the tour guide's dad played shortstop on a church team that would enter the prison to play against the prison team.
Pontiac, IL is a really nice small town with murals on nearly every wall.
This is the second stretch of Route 66 that I've done, and it's a weirdly social experience. There will be other people driving Route 66 at the same time you are, and they will stop at the same attractions along the way at roughly the same time. You might as well talk to them, or else you'll just awkwardly see each other all day in silence.
