Check out Cape Cod. By September most of the tourists have left so it shouldn't be so crowded and the weather should still be OK. I recommend Falmouth down on the south end of Cape Cod or Chatham and the National Seashore on the eastern edge.
**Bump** So, I ended up not being able to go on the Boston trip back in 2015 but I am for sure going next week and have tickets to see the Astros play at Fenway, pretty stoked. Anything changed in 2 years that I should check out?
Make sure to stand up at Fenway and yell, "Nomar (pronounced 'Nomah') is wicked good" over and over. The fans will love you there if you do that.
Go get a lobster roll at Pauli's (next door to Neptune). They jam pack it with so much lobster. https://www.yelp.com/biz/paulis-boston Mike's Pastry is overrated.
Driving IN Boston is even a bigger nightmare WITH a GPS. Boston streets take every form other than straight, and that coupled with tall buildings means that a GPS will fail to register the correct street that you are on. I'd rather drive in Manhattan. But it's worth it........awesome city (just not to drive in unless you've been there a while).
I got a hell of a deal on a rental car $9.99/day with enterprise & this might be my biggest fear. I am staying with family in Rowley which is a 30 mile drive north and ill be making treks south into the city that entire weekend.
[BUMP] I’ll be headed to Boston the first week of September. Already got tickets to the Sox and Yankees game. Looking for recommendations on the best area to stay and any other recommendations as far as food, entertainment, experiences, etc. Thanks in advance!