Milwaykee to Virginia ?
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Mapquest routes you through Indianapolis. Pretty boring, but if all you want to do is a straight shot, it will work. Not a lot of scenic riding between here and there regardless of the route. From Indy east you could probably find some better 2 lane if you were so inclined. Of not, I would just kill that ride off in a day (says 12 or so hours) and be done with it. The riding in VA is pretty nice.
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Now Nevada, I have to disagree. Find yourself a route to southern Ohio, take US 50 across Ohio, thru West Virginia and into Virginia. There are lots of scenic roads in southeastern Ohio and in West Virginia along the way. Just depends on the time constraints. If you're looking to beat in the road, take the interstate, if not, take the road less traveled and remember, you are only one wrong turn away from your next greatest adventure.
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Cheryl and I did your famous triple nickel down to 50 and rode it out to DC. It was very nice and I highly recommend - if you have the time.
If the Blue Ridge Pkwy is any indication, the deer are active dusk till dawn and then some.
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If you've got a little time, drop down to Columbus OH and instead of taking 50, go a little further around Columbus and take 33 down and across OH and WV.
At Elkins WV, take 219 down to 39, turn left on 39 and go to 42, turn right on 42 and take it down to I-64 for a short run to Lexington.
At Elkins WV, take 219 down to 39, turn left on 39 and go to 42, turn right on 42 and take it down to I-64 for a short run to Lexington.