Warrenton, in Fauquier Co., is a cute town. I wouldn't rule out living there or further west. The commute from Winchester to Fauquier isn't that bad on 66 (45 min.) - I've done it a few times. It's commute from Fauquier Co. to DC - now that gets a little sticky.
The Winchester Wheelmen usually have a pretty high male/female ratio when we road ride. Everyone is welcome.
www.winchesterwheelmen.org.
Is anyone doing the MS 150 in Charlottesville?
On another subject, any ideas on living arrangements in Alexandria? I am job hunting in that area.