Kevin, you will LOVE Boston! It's a great town. Don't miss the Freedom Trail if you like history. It's probably ridiculously pathetic history compared to yours, but it's the best we can offer over here!
Now, this is important. In Boston is Harvard Square, an interesting place near the university which is great for people watching and catching street performers, many of them quite excellent. Just around the corner from the square is this little place in a basement called Club Passim. It's a kind of open mike place where anyone can come in. Who comes in are the folk singers from all up and down the Eastern seaboard, the stunning new artists studying at Julliard, and the amazing students from Harvard U. Borrow a guitar and put your name in for the open mike! There were a million people the night I went (well, 34 people had signed up before me) so they never got to me, but the entertainment was great. Some of these people are unbelieveably good. More: http://www.clubpassim.org/
My brother-in-law lives there. I'll ask him for recs for places to eat etc. if you'd like it. (Perhaps Matt will do as well.) I was there for a business conference, so I didn't get to see much personally. I want to go back!
You'll have to let me know your impression of mainland America. I hope we are well behaved! Have a great time!