We're up in Lenox, MA (from NYC) six or seven times a year and have been in constant search for a good restaurant in central or southern Berkshire county, and we've finally found it - Nudel in Lenox. Wheatleigh is good, but uber pricey and I've heard good things about Old Inn on the Green in New Marlborough, but Nudel is the best moderately priced placed I've tried in the area.
The menu changes nightly and is seasonally driven and, when possible, locally sourced, so recommendations on particular dishes will be moot. But, having gone twice in one weekend, I have to say that the chef, Bjorn, is very talented. His two preparations of octopus were phenomenal, and he worked magic with local radishes. Spaghetti bolognese with bone marrow was fantastic, as was Yukon Gold gnocchi. Braised octopus, octopus and mussel tacos, radishes with soft polenta and BBQ ribs with cheddar grits were all fantastic.
It's a small place, no reservations, and it caters to foodies for sure, but approachable and affordable. Highly, highly recommended. For the money, compares with my favorites in NYC even.
11 Hawthorne Road, Lenox, MA