I actually grew up riding the W&OD. We lived in Falls Church when I was in elementary school, and I used to ride my bike along the W&OD to get to a comic book shop on Route 7. Then, when we moved out to Reston and then to Herndon when I was in high school, I rode it out there. Now, though, I don't go farther east than Goose Creek. Waaaay too crowded for me down thataways.

Would Leesburg be too far west for you to start a ride?