Arminius from Richmond, VA on 3/11/2020 1:37:25 PM:
I agree with John from Pittsburgh, but in the opposite direction!
Living near and visiting DC a lot, I prefer to head towards Pittsburgh as west to east seems anti-climactic. Remember, the elevation gain is not that much and it's spread out over hundreds of miles. You really don't feel the elevation gain going west, at least up to Cumberland.
In terms of winds: generally, the prevailing winds are W-E, with some NW or SW variance. Sometimes it doesn't matter. One trip, I left Mt. Vernon in a 30 mph headwind. It didn't let up until I got to Brunswick where I camped. 70+ miles into that wind sapped me of any energy I had left!