Make your reservations early if you need a place to stay. There will not be a hotel block. We highly recommend getting a room for the overnight of the 600k even if you are planning on riding straight through. Having the option and a place to shower and change/keep clothing and devices charging makes everything easier.
Moderately challenging 400k from Woodstock with a few hills at the start. We head west to Oregon on some flatish roads to build up a time buffer, then north up through Pecatonica to Brodhead then New Glarus. You can take the Sugar River Trail if you don't mind a gravel/hard pack trail (the GPS takes the roads) from Brodhead to New Glarus but beware - 2 riders have broken bikes on this trail (a fender and a rear derailleur). From there we head east back through Evansville and Milton before heading south through Darien and back to Woodstock.
This is an official PBP qualifier.