Amhearst and Burlington
In Amherst, Judie's is solid (creative American faire). Chez Albert (French) is also supposed to be good, but it's a little on the pricey side. The college kids love Antonio's for the pizza. I'm not crazy about it. Black Sheep has decent sandwiches. Bueno Y Sano has great, cheap, healthy (but not very authentically Mexican) burritos.
Northampton is nearby to Amherst (11 miles or so) and there is a ton of food options there. Search this board for Northampton suggestions. My favorites in Northampton are Circa and Osaka.
In Amherst, the Lord Jeffrey Inn anchors the commons, it's a beautiful old inn, very convenient to everything (and a bit pricey). Not sure of their dining.
Antonio's Pizza is excellent if you're in the mood for a quick slice (notwithstanding the unenthusiastic mention by stephan). They have about 25 different types by the slice and the slices are giant. They use good, fresh ingredients. Potato & bacon, blue cheese & chicken, black bean & roasted pepper, plain cheese sicilian, etc.
Judies is, well, one of those restaurants that found its niche and never stopped. I guess you could call it solid. It's amazing, it's been in the same spot since I was at UMass in the late 70s! I'm not sure what to attribute that too - certainly not dining excellence. Perhaps just familiarity, a busy college town location, and reasonably decent food. If you're looking for something creative or interesting, I wouldn't try Judies.
Antonio's is good for a quick slice. Only been to Chez Albert once, enjoyed it thoroughly, but it is basic bistro fare. There's a great Pho place in Amherst sort of tucked in behind the main business block.
I suggest Northampton, where you can try Circa before the current owners complete their sale and move back to California. Also, I have friends and family stay at the Autumn Inn across from Smith College. Pricey, but anything else in the area that's acceptable is too, including a relatively new Hampton Inn in Hadley, between Northampton and Amherst.
I ate at Lord Jeffrey in Amherst once and I was completely unimpressed. It's a tourist trap in my own personal opinion - and an expensive one. I wasn't so thrilled with Judy's either. Antonio's pizza is awesome, but it's not a place to really sit and relax. Bueno y Sano has the best burritos I've ever eaten in my life!
In Northampton the East Coast (or East side) Grill is good, La Veracruzana is very casual but good, I used to like La Cazuela, but I don't know if it's still in business.
When we did the college tour thing a few years back, we also ate at Antonio's in Amherst for lunch and thought it was quite good. In fact, our thinking was that it's not worth going to college in a town that doesn't have decent pizza, so we ate pizza virtually everywhere, and Antonios (both in Amherst & Providence) was the favorite. I've heard that the pizza at American Flatbread in Burlington is good but never tried it. For an upscale meal outside Burlington, go to Starry Night Cafe in Ferrisburgh.
Had a decent Chinese meal at A Single Pebble on Bank St. last summer.
My all-time favorite place in Burlington is Bove's. I've been eating their meatballs for about 30 years (gosh, that makes me feel old). They are fantastic. There's nothing fancy about the place, just terrific red sauce Italian family style meals.