So, after some discussion and deliberation, I've decided to go forth and do both a DC to Pittsburgh Bike Trip as well as a new Erie Canal Bike Trip this year. The Erie Canal will go from 25 June to 1 July, while the DC to Pittsburgh will be from 5 to 10 July. The posts below describe both trips in greater detail.
Comments about the Erie Canal Bike Trip: We live in Rochester now, so this makes a bit more logistical sense. The Erie Canal Bike Trip is about the same length as the DC to Pittsburgh trip. The trail is only 75% complete, so there is some riding on roads. The area is more developed, though, meaning that trail/road surfaces are better and you are generally not "in the woods". Also, as I have only biked this once, this trip will have a more flexible schedule than the DC to Pittsburgh trip.
Comments about the DC to Pittsburgh Bike Trip: I've scheduled this trip around the 4th of July on purpose. As many of you know, I need to be in DC every year on 3 July evening to help operate The Traverse. This scheduling also allows folks from out of town to come to DC early to join me on The Traverse (or just watch 4th of July fireworks) before the bike trip starts on 5 July afternoon.