I could set up a cruise on some pretty cool roads down there. Still know them like the back of my hand. There is not much in Chester besides a statue by the bridge, and a nice Max. security prison just down from there.
http://www.guide4chester.com/popeye.html
Between Steeleville (my home town) and Chester is an awsome covered bridge, that in the last 10 years has been restored. Makes for great pictures.
http://www.texasescapes.com/Illinois-USA/Marys-River-Covered-Bridge-Chester-Illinois.htm
Pyramid state park, is over by DuQuoin, quite a drive from chester (45 min.) Piere Menard home and park is close to chester, with an impressive plantation home. As well as Randolph county lake, but I have heard they are not mowing most of the park area due to budget cuts.
http://www.illinoishistory.gov/hs/pierre_menard.htm\
There is a small town down there called Shiloh Hill. (between Steeleville and Chester on a different road) First collage in Illinois is located there. It consists of the old college building and about 10 houses and one of the best little bars you will EVER find. It is legendary in the area for it's pickled eggs. It is my wifes uncle, who swears he will die with the recipie. Kerry, they still have shooting matches out the back window of the bar.(still target of course, no jug guns)
If you continue farther south towards Carbondale and Macanda, there is a winery trail.
http://www.blueskyvineyard.com/
http://www.shawneewinetrail.com/
I know the area very well. If you guys get serious, the best time to do this would be the fall, as the Shawnee hills, get very beautiful.
Let me know if there is any interest, I would be more than happy to help out. I spend the first 23 years of my life 10 miles from Chester!
The worst thing is alot of the roads are oil & chip.
(Mike, these are the old, Beast light bottle, drinking roads!)
