BamaVol, if you are visiting Pittsfield and want to head out Worcester way, I will be glad to buy you a draft or two at
the Boynton in Worcester.
Draft list in pdf form here . Over 55 beers on tap with a good selection of seasonals. Had some folks visiting from Prague and took them here and they had a ball trying all the different local brews from Berkshire to Wachusett to Shipyard. BBC's Steel Rail Pale Ale is my usual, but I have been know to quaff a Guinness or two or a Smuttynose Old Brown Dog Ale.
Another spot I bring visitors to is Peppercorns in Worcester for the
Wormtown microbrewery out back. They have a huge selection, not 50 but they have lots of seasonals and almost one of every kind of beer you can think of. They make a point of including Massachusetts ingredients in every beer.