I'm a North Berkshirite who has benefitted for years from hounds around the northeast when I travel, but I've not seen anything all that helpful about my own neck of the woods. So, for what it's worth, here are some reflections on the dining scene in the northern Berkshires (with occasional forays a bit further afield):
The best serious restaurants in the area are Mezze in Williamstown and Gideon's in North Adams.
Mezze has varied somewhat over the years depending on who is the chef, but the food has been constently excellent over the past year. Menu rotates so it is hard to recommend anything in particular, though this is a better place for meat (including poultry and fish) eaters than pure vegetarians. It's not really a place for mezze--there are assorted small portions and side dishes, but this is really a traditional main dish place and not a small plate restaurant--but it *is* a place for imaginative and well-prepared food. I guess you'd have to call it eclectic New American, since I'm finding I can't really comfortably place the food in a particular regional or ethnic tradition.
I guess you'd have to five the same designation to Gideon's, where the food is consistently fine, too. I especially prefer the Peking duck spring roll (even better than the--excellent--comparable roll at Jae's) and the Asian Sea Bass (which comes on and off the menu), but I've not had a bad dish there yet.
The food at Jae's, a pan Asian place in North Adams related to the popular chain in the Boston area (Jae is a North Adams native who opened his place here after success with the Boston joints), is also of consistently good quality. Best Sushi in the area, excellent appetizers; I also like the Korean dishes a lot. If you're looking for the kind of hardcour authentic food for which you'd scour Koreatown in Manhattan or the places in Queens (or fill in the blank for your favorite enclave for Chinese or Japanese food), you'll be disappointed. But if you take Jae's for what it is, you can have an excellent dinner.
Jae also now owns Williamstown's Le Jardin, one of the fancier and more expensive restaurants in the area. Execution is generally good, but the concept--in everything from decor to the menu--is essentially "French Food" as Americans imagined it in about 1965. If that's your thing, you'll have a fine meal; it's not mine.
Cafe Latino is now at MASS MoCA in the former site of Eleven. Both menu and decor are different, and both are notable improvements. Cafe Latino is owned by the same people who own Mezze, and the chef, Omar, is that restaurant's original chef from its early glory days. The restaurant is well-named: this is culinary latinidad, not the food of one ethnicity or nation or province. But with a few exceptions (strangely bad Guacamole and rotten beer list), this is a good place. By far the best food, I think (at least for carnivores), is to be had in the various "family style" dishes that serve 2-4 people. Go with a decent sized group, order several of these dishes, and you'll have a great meal. Excellent patacones and the pork sandwich are also highlights.
One of my favortite places around. Small, intimate, comfortable, unpretentious setting. Good service. Another eclectic menu that is hard to classify (a French-style dish here, mussels in coconut milk there, etc.). The food is not quite as interesting as at Mezze or Gideon's but this may still be the most pleasant place to have a meal.
Good "Ethnic" Food
The oddly, but accurately, named Sushi Thai Garden, on Spring St. in Williamstown, serves respectable Thai food and pretty good Sushi. Very nice people, efficient service, reasonable prices. If you're from a big city with good food this won't blow you away, but it's way better than Asian food used to be in rural New England and its a mainstay for those of us who live here. Everything's a bit sweet, and the spicy dishes could be a bit spicier, but there also isn't a bad dish on the menu. I like the Gai grapaw (minced chicken with basil and chilis); and if you like Pad Thai, it's actually unusually good here.
Spice Root, an Indian place next door to Thai Garden on Spring St., is also a solid, professional restaurant that is friendly, reasonable, and well-run and that is both better nothing to blow away someone from a city with a large Indian population and better than you might expect in rural New England. Great, fast, inexpensive lunch buffet, too.
Coyote Flaco opened recently. It's run by an Ecuadorian couple who (I believe) also own the several places of the same name in Connecticut. It opened this spring (06), and after a slightly rocky beginning with horrifically slow service, has hit a groove. The owners are personable and attentive. The permanent dishes are not surprising but all that we've had are good (Oaxacan style enchilladas are very popular with my family), and the specials, particulary the meat specials, are often very good, too. Tasty, and immense, Margaritas on offer as well.
Hickory Bills in North Adams is a little operation serving Texas style BBQ. I'm not from the South and so my standards may not be the most discerning, but I find the food quite good, particularly the ribs and the collard greens. Bill himself is a trip and a half, oscillating pretty widely between quite grumpy and very friendly, often over the course of your meal. He's part of the show and a reason to go.
La Fogata in Pittsfield. I've not atttempted to review the--growing and increasingly interesting--restaurant scene in Pittsfield, but I wanted to put this simple, unpretentious, delicious Columbian place (restaurant, store, and hub of the local Latino community) on the list.
Good lunch bets:
Helen's on Spring St. in Williamstown: excellent sandwiches and a wide and shifting array of salads (tofu ginger, bean, Asian chicken, etc., etc., ) available to go or at a limited number of tables.
Both Thai Garden and Spice Root are quick and inexpensive for lunch.
Jack's is a famous hot dog stand in North Adams.
Weakest meal in the area. There simply is not a GREAT breakfast spot in the North Berkshires.
The Chef's Hat is probably the best bet in WIlliamstown. Typical breakfast diner. I like the place but it's not memorable. (If you want real maple syrup, remember to ask for it.)
Miss Adams Diner in Adams has a bit more kitschy diner character, though the food is also not really special.
For an awesome diner breakfast, head up to the Blue Benn in Bennington, where you can have everything from the traditional stuff to assorted vegetarian and Mexican-inflected items. Real character, excellent food, and long waits for a table are all part of the experience.
The above mentioned Le Jardin is now doing weekend brunch, but I've not been. (So maybe THIS is the great breakfast spot, but nobody's suggested that to me.)
There is a huge, fairly expensive, brunch at the Williams Inn on weekends, too. The selection is vast but the food is not outstanding--this is basically where New England food was a couple of decades ago, when food like most of that described above was not yet available in these parts.
I've left off a lot of places, mainly because I like them less than those above. I've not wanted to spill a lot of ink dissing local places, but I do have to say that for Mexican food you'd have to be desperate to go for Desperados (Coyote Flaco is several cuts above) and that the popular Water St. Grill has always struck me as having the worst price-to-interest/quality of food ratio in the area.
Hope this is helpful.