Just chiming in here....
Some of you talked about the need to have Galena locals maintain a trail at Chestnut once it's built.
I don't know if there is an organized group of bikers in Galena per say, but there is a semi-organized group of riders & maintainers in Dubuque, 20 minutes west of Galena. They maintain FDR park trails (which are awesome) in Dubuque and have a Facebook page, "Friends of FDR Park."
THOSE folks from FDR park might be willing to regularly maintain a trail out at Chestnut once some folks from Chicago do the initial build. Or maybe it could be a Dubuque/Chicago joint effort--- Just a thought.