I've spent the last 25 years of my life (aka my entire life) in the Phoenix area. Fiance is from W Mass (Agawam/Springfield), and we'll be heading back east for the Big E and a friend's wedding in Boston.
When we plan vacations, I typically make up a food itinerary for the entire trip. While he appreciates a good meal, he's hardly as obsessed as I am, and just goes along with whatever I say. However, since he's so familiar with his area I'm kind of leaving that portion of the trip up to him. (To give you an idea, he's most pumped for White Hut and ice cream at Friendly's.)
I think my biggest question is what to eat while driving to/from/in Boston. I am hoping I can convince him to a nicer sit down brunch/lunch the day after the wedding before we drive back to Springfield. I'd LOVE to do Neptune Oyster House, but the guy doesn't eat fish. A friend also recommended Toro, which I know he'd go for, but I was kind of hoping to make it somewhere more "New England." We're staying in what the hotel calls "downtown Boston," but we will have a car.
We're also driving up to Amherst and Northampton at some point, and any specific recommendations about the Big E would be appreciated. Also, is it too early for apple picking? Every fall I read about these apple cider donuts on every single food blog, and I'm dying to have one. Oh, and aside from the detour in Boston, we'll have our two youngsters with us. :)