I just got back from 3 days in the Berkshires (my first time there). Here's where we ate:
Bizen (Great Barrington): This place has an enormous menu, including many unusual sushi combos. We had sort of a mish mosh of things: edamame, steamed tofu dumplings (that were peculiarly reminiscent of blintzes), soba with tempura shrimp and veggies, and crab and avocado inside-out rolls. The dumplings had a sour flavor and weren't to my liking. Sushi was very good, and the soba was great except for the fact that the delay in serving it caused some of the tempura pieces to get soggy. The service here was haphazard, but I found that to be our typical experience in the Berkshires.
Bev's Ice Cream: I tried this because of a recommendation on the site. Fine enough, but nothing spectacular.
Old Inn on the Green: We were there for their Saturday night prix fixe menu ($58, I think). The place was charming and the food delicious. I especially enjoyed my main course of poached lobster served with grapefruit sections, orzo, and peas. It may sound like a weird combination, but it was delicious, the kind of thing you keep eating even though you're way full. Our appetizers were good, too. I had a mixture of wild mushrooms served with a puff pastry. My husband hat a grilled prawn served with asparagus and lentils (the lentils were exquisitely prepared). I was disappointed with the dessert selections, as there was no chocolate choice. When I voiced my complaint to the waiter, he offered me their homemade Belgian chocolate ice cream, an offer I accepted. My husband had a frozen lemon-orange souffle cake, which was just okay.
Once Upon a Table (Stockbridge): Good for lunch, and probably the only place in town that has decent food. We had a bowl of clam chowder, a Caesar salad, and crabcakes. All were good, none outstanding. However, their creme brulee was delish. The staff here was very, very friendly.
Spigalina's (Lenox): This place seemed overrated to me. The atmosphere is poor (we were seated in a room that felt like a hallway, with lots of foot traffic streaming by) and they were understaffed. We had a decent appetizer made up of assorted vegetarian dishes. My main course, a butternut squash risotto, was way too rich, and the butternut squash had the consistency of a potato, not of butternut squash.
Bistro Zinc (Lenox): I had a DELICIOUS egglplant sandwich here for lunch. The eggplant was so crispy, yet still very tasty. My husband enjoyed his smoked salmon sandwich a lot as well. Our waiter was very well meaning, but more or less incompetent. We were fortunately in no rush or we would have been very frustrated.
Verdura (Great Barrington): I'm saving the best for last. We LOVED this place. The setting is very warm and rustic. The food was outstanding, certainly as good as you'd find in any big city. To start, we shared a minestrone soup (a special that night) and a chickpea flatbread flavored with oregano and olives, served with Bufalo ricotta from a local farm. I'm getting hungry just thinking about it. Then I had tagliatelle with wild mushrooms and black truffle oil. My husband had a gnocchi dish served with root vegetables (carrots, parsnips, celery root) and cooked in a vegetable demi glace. I haven't seen him enjoy a dish this much in many months. He sopped up all the remaining sauce with a piece of bread, and even joked that the restaurant wasn't THAT far away from New York City (where we live). (I think he was trying to figure out a way to return.) For dessert, he had a tart tatin and I had a delicous cannoli filled with sheep's milk ricotta (also local).
I think that covers everywhere. Hope this helps Chowhounds visiting the Berkshires in the coming months.