Thanks for all the replies! That Chicago suggestion is tempting the more I think of it, and I hadn't considered non-Manhattan NYC. I've only visited with friends/family and they all like to stick to the guide book.. ugh. Those mentions of New Orleans food are speaking to my empty stomach right now. And Boston is a total unknown to me so I'll have to investigate.
I was actually out in D.C. just last week and loved what I was able to see! Too bad work got in the way of all my fun except for a couple quick jaunts. It's on my revisit list for sure.
All in all, I think my thread to narrow things down has done the opposite. You guys are so helpful!
I can set you up with all the Chicago info you want. That city was my home for 42 years. Contact me off line if interested.
You might want to re-think the assessment of Toronto as being cool - I was there the last weekend in June and it was around 95F every day.
Today was in the mid 20'sC so it has cooled down from the end of June. It is a little on the cool side for this time of the year however but should be nice around September. We will not likely have fall colours yet, it is too early, but to enjoy them you are likely going to want to get out of the city anyways and that will require a car, which you will not have.
Southwest doesn't fly to our neighbors in the north. It is a place I'd like to see at some point, though!
Again, thanks for all the suggestions. My little weekend excursion keeps growing in my mind and it's going to end up some epic adventure. One thing I've come to realize is that we're pretty spoiled when it comes to having a big variety of accessible destinations.
"Technology is a big destroyer of emotion and truth. Opportunity doesn't do anything for creativity. Yeah, it makes it easier and you can get home sooner, but it doesn't make you a more creative person. That's the disease you have to fight in any creative field.. ease of use." - Jack White