OTOH, by the time you hit central - east Texas, you can probably mail all that stuff home and pick up the pace.
(Reverse if you're riding east to west -- plan to have someone ship camping gear to you in Texas!)
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One reply suggested the W&OD to Front Royal, Va.I drive the route over the mtn on rt 50 or rt 7. Both are major high speed commuter routes with narrow to no shoulders. I cringe with horror when I see a touring cyclist on these roads. I have considered stopping to offer a ride up and over, but there is NO place to pull over. There are safer times to ride these routes, but still expect high speed traffic.
The Northern Tier has fewer mountain passes than the Trans Am, and they are generally lower in altitude.
Another data point: our Prius hatchback has held two people, two road bikes lying flat with front wheels off, and luggage for a two-week supported trip & visit to family comfortably. Inserting that second bike did take two people.
... no likelihood of the brakes overheating the rims and blowing a tire.
If you're pressed for time, you can skip Yorktown and join up with the TransAm in Richmond.
I don't remember any campgrounds or water sources after Colonial Creek. As Fred pointed out, you might luck out and get water from people in cars. And if you have a water filtration system there are numerous streams you can use. There is a pit toilet between Rainy and Washington Passes, but no water.