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My parents used to live in Stockbridge but haven't for a few years so my info may be out of date. But there used to be a Greek-type restaurant on Rt. 7 on the "strip" just south of Pittsfield -- maybe Sofia's or something? - unpretentious, just good chow. Good Greek salad, excellent crab cakes. Right across from Friendly's in case the kids want ice cream.
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On Railroad Avenue, right off Main Street, there is an excellent homeade ice cream place which I go to every summer. It used to be called Bev's but I was just there the other day and they changed the name. It is next to Bizen,by far the best Japanese restaurant in the area- not the kind of food you are looking for but something to keep in mind for another visit.
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A couple of suggestions...
Our ABSOLUTE favorite restaurant in the Berkshires is the Castle Street Cafe, just around the corner from the main drag in Great Barrington. Besides wonderful "casual new american," it also has things like burgers and pasta. How old are the kids?
A more casual place is a brew-pub on Route 7 in Gt. Barrington, just called The Brewery I think. I haven't been there in a while but it used to be very family-friendly, with good basic chow.›1 Reply-
re: checkman
Unfortunately, Jiminy Peak is north of Pittsfield, so Great Barrington might be too much of a haul.
A great option in Pittsfield with kids is Elizabeth's, which a casual and very good mostly (but not exclusively) pasta restaurant. They fill up on weekends, so reservations are a must. For ice cream, there's a Ben & Jerry's on Route 7 in Pittsfield: not homemade, but good nonetheless.
On Route 7 between Jiminy Peak and Pittsfield you'll find a handful of roadside shacks selling ice cream and other shack-like food. I have no idea, however, how good they are.
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