speedster on 6/22/2012 11:14:19 AM:
My preference is to proceed eastbound from Cumberland. The prevailing slope is downhill (if only slightly), but over that number of miles you'll descend about 500 ft versus having to climb that same amount.
Also, prevailing winds tend to originate out of the west to southwesterly direction, so you'll have a pushing tail wind versus a headwind to push into. All in all, this makes this the better choice in my estimation, unless you reside around DC and prefer to start from your home area..