Well, I'm guessing the caravan will consist of Janice's car and your car, unless we can fit all three bikes on Janice's car and she drives all three of us together. The three of us can meet at Bike Dr to head down to Va. I'm guessing 9:15-ish to be able to get down to Leesburg by 10:00.
I usually get on the W&OD trail in Leesburg where it crosses Harrison St, but I noticed the last time I parked near there that the lot I use is supposed to be only for the Parks Dept so I don't know if we want to try that. If it's just the three of us, we can park on the street or in one of the parking garages in Leesburg and cycle over. If we're meeting your friend, though, she might be able to recommend a better spot to meet/park/start riding.