So I'm thinking about taking a week off work and doing a one week roadtrip either with a friend or by myself. Preferably with a friend, but I'm having trouble thinking of things to do. I'm in the southwest region of Virginia and this won't be until June or July but so far Chicago and New Orleans are on my radar. I figured I would open it up to the community to suggest places or things to do.
When I was a small child we lived in Manitoba which is pretty much the center of the continent. We managed to road trip to Newfoundland and back in two weeks, going through parts of Ontario, New York, Maine, Vermont, New Hampshire, New Brunswick and Nova Scotia. My point is that you can probably go farther in one week than you think.