Bloomington, IN

Should I go to Bloomington, IN? Is it worth it? My family knows people in Bloomington so I might get housed there. Then I heard about Richmond, VA being a good traveling kid town, or it was somewhere near Richmond? Tell me some awesome places to stop at between those spots? I live in Huntsville so I'm plotting out a triangle of sorts.
 
Definetly I'm out in ny right now kinda stuck here for like 1 more weeks trying to take care of some stuff then I'm taking the bus, after that back on the road man, where are you at now? how long till you get there?