My family and I got back from a Berkshire vacation two weeks ago. Since I have two small children (one a picky 7 year old, one a baby), our choices for dining skewed toward the family-type places. Also, we stayed at the Vacation Club In the Berkshires complex near Jiminy Peak, so we had a full kitchen to work with.
Our first eating experience going in -- was Friendly's in Pittsfield (rte. 7/20). Why? Because we arrived late, and the places open after 9:30 pm are few and far between. That said -- Friendly's is reliable and kid-friendly (even if all the kiddies fell asleep in the restaurant).
The next morning, I headed out for grocery shopping and wound up at Guido's. I love, love, LOVE Guido's -- it's like Whole Foods, but without the pretension (the prices can be as high, however). Great selection of cheeses, breads, deli-meats, picnic items, meat, fish, fruits and veggies. I spent waaayyy too much money there, but found some Berkshire pork chops and killer lamb chops for in-home dinners (with kids, you have to create your own fine dining experiences outside of restaurants). I cooked them later in the week, and we enjoyed every bite (even my 7 year old). I also loaded up on local corn, blueberries, and peaches from farmstands, and some less pricy staples at a local grocery store (cereal, juices). We also tried the Highland Farms milk from Guido's -- very rich and tasty.
We had a few eating out experiences, after Friendly's. One day, we traveled up to the Blue Benn Diner in Bennington, VT. Great place, great breakfast. We shared one of their homemade cinnamon rolls. I had sausage & biscuits, while my wife had blueberry pancakes with bacon and maple syrup (at extra cost), and my son had french toast with sausage (the baby had a bottle). Not a scrap was left at the end of the meal.
Another day, on the way back from the Norman Rockwell museum (highly recommended), we stopped at the Misty Moonlight Diner in Pittsfield. Next to impossible to find, but it's worth the search. Great 50s Decor -- well done. My wife had the meatloaf and mashed potatoes with gravy -- the meatloaf was moist, the potatoes were real, but (alas) the gravy was canned or prepared from a mix. Real gravy is the best, but hard to find. I had a bacon cheesburger with onion rings, with a beer from Berkshire Brewing Company (yes -- the adult Happy Meal). It passed my test on all fronts. My son had cod fingers and fries, with chocolate milk -- although we had to take something home, it was eventually devoured. The baby had another bottle.
We spent a day at Jiminy Peak's Adventure Park (my son, my wife and I loved the Mountain Coaster), and then had dinner at John Harvard's (on site at Jiminy Peak). I've been to John Harvard's in Framingham, and I was not disappointed with this version, although the beer tends to stand out more than the food. I had a chicken-BBQ-bacon sandwich, fries, and John Harvard's version of summer ale (Summer Blonde). My wife had the orecchiette pasta with chicken and sausage, with a rassberry ale -- I took a taste, and it seemed cooked al-dente, with a pleasing blend of garlic and wine in the sauce. My son had chicken fingers and fries, and the brewed root beer. The chicken fingers were cookie cutter, but the root beer is worth a try.The baby had -- guess it -- a bottle, as well as tons of fun with our unused spoons.
Our final stop (for a lunch) was Burger, on North Street in Pittsfield. This is a O.K. Chowhound place -- spacious, with a limited menu and focus. I wish that the regular burgers were a little fatter and juicier (I had a better burger at Moonlight Diner -- these reminded more of steamed burgers than fried burgers). The fries, however, were killer and the chocolate milkshake smooth, tasty and cold. My son's chicken fingers were anything BUT cookie-cutter -- they had been fried with a crunchy coating and my son had to guard them carefully (from me). My wife had a BLT, and enjoyed it. The baby had his bottle, but looked enviously at our food. If I went back, I might spring for the Kobe Burger and the eggplant fries -- very interesting menu items in a burger joint.