I am definitely down for a straight up 100 mile ride. Let me lay one on you.

Google maps is acting up so I will lay it out verbally: meet somewhere at buttcrack of dawn-thirty. Let's just say the bean downtown. Proceed west on randolph, south on halsted, west on washington (for a looong time). intersect butterfield road, proceed to illinois prarie path. Take prarie path to wheaton until prarie path elgin branch. Take parie path elgin branch into the city of elgin.

Now here is the part I need help with...get from elgin to northbrook velo in 25-40 miles. Definitely doable, I know there is a trail out there...but where?

Proceed to velodrome. Go south on waukeegan, west on willow, turn south on north branch trail. Take north branch trail south to elston, take elston back downtown, or until the official computer hits 100 miles.

I gmapped this and it will be 100 miles easy. Plus there are a lot of trails, so very little braking.