Road Trip (Going solo)!

I'm just beginning to make plans for a late summer road trip on the motorcycle. The outbound destination is to visit my brother in Vermont, but truthfully,  it's as much about the long ride as it is about the destination.
I have yet to get into the habit of making stops along the way. I'm usually happy to be on the road. For this 3,500 mile trip, I'll need to be more aware of places to stop and things to experience.

I have a few ideas of places I'd like to travel through along the way, but still need to work out a suitable plan. A few things on my list of potential stops:

Chicago (to see the kids)
Cleveland Indians baseball (they're in Cleveland on my outbound journey)
Pittsburgh for UFC Fight Night (this would be on the homeward journey)
A wide swing through Portland ME and Providence RI just to add a few more states to the trip.
Springfield VA for lunch with blogging friend
Deals Gap NC to ride the Tail of the Dragon (318 curves in 11 miles)
Return route through Louisville KY (again to add another state)
Cicero IN for an overnight visit at my sister's home.

Obviously, I am not going to be able to make all of the stops or detours for the sake of checking states off my traveled through list. Although Cleveland works well for being on the way, it isn't really where I want to stop for the night (it would be a pretty short travel day) and so I need to figure out how to secure my travel pack while I watch a ballgame.
A detour through Louisville would mean skipping the overnight at my sister's place near Indianapolis. Actually, Louisville isn't a detour if I make the run to ride the dragon.

For now, everything is just an idea or thought of what might be. I wouldn't mind stopping in NYC but since I know I won't have much time and I'll be on the motorcycle I think I'll pass this trip. The UFC Fight Night isn't a great card so even though I'd love to see it, it isn't a really big deal. I've also considered bypassing Cleveland to travel on the Canadian side of the lake and visit our friends near Toronto.

A few days visiting with my brother at his lake cabin will be a nice break to the motorcycle travels. I'm looking forward to a little kayaking, a good visit and the serenity of the lake setting.

If anyone has thoughts or suggestions, feel free to comment. I expect to be on the road beginning around the 6th or 7th of September and back around the 19th or so. I am enjoying checking out the possibilities and looking at the map to see where the road might take me.

John <><