Assuming permits/etc come through again, here is what is was last year:
http://wisconsinmilkman.com/course/

For hotels, the Sheraton and Holiday Inn on John Nolen are ground zero for the race, but not really walkable to Madison's to-dos. Something on the square, or just off like the Hyatt on west Washington or the Hampton inn on Johnson/Bassett are probably good bets.

For food, just kind of depends on what your jam is. Food scene in Madison punches above it's weight for a city it's size. Tons of great options downtown or on Williamson (Willy) street.