if it weren't for the allergies:
Louisville ky. 100 mile bike/run loop around town, which currently is about half completed, with the longest connected section ~36 miles.
xc is great at tom sawyer, site of ncaa natties
Frederick law Olmsted designed park system downtown
kinda hip if you live in the highlands or saint Mathews or near Cherokee park
indoor track planned on being built in the next 5 years
wish there were more soft surfaces though