Never done 55, but If I were gonna consider 250/220, I'd head up towards Harrisonburg and do 33 to 220 instead. 250 along the National Forest is fun, but hairy. 33 is slightly less hairy, better road overall, and has more places to pass. [/hijack]
Thanks BT! Google suggests that I would shave 40 miles off my trip by taking 250 or 33 to 220 instead of 55, and take just as long (4:30). I think I'll go the way I know best (55) since it is gonna be a late night drive.
BTW - 55 is becoming part of the "Corridor H" project that is sloooowly creating a highway from I-66/I-81 to the Canaan area.
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