Tim,
I'm sure Steve Curry will chime in as the resident expert on the Pittsfield area.
I've heard conflicting stories of who designed CC of Pittsfield, either Donald Ross or Styles and Van Kleek. The club claims Ross was their designer in 1917.
The golf course is fun. A lot of elevation changes and interesting green complex placements. The drive off the 10th tee is a gorgeous view of the mountain backdrop to a fall away fairway. Greens are very slick. Not many level lies. The views are spectacular, but that's true of most courses around the Berkshires.
Brad Benson is the long time resident pro and a good guy. I'm not sure what their guest policy is nowadays.
Depending on where you will be, other courses to check out:
North County: Taconic (profiled and discussed here often) and Waubeeka (not high on architectural merits but stunning views on Route 7 just south of Taconic).
Central County: Berkshire Hills CC in Pittsfield is a neat course (Steve Curry's place and a Tillinghast design, I was a junior member there many years ago), Wahconah Country Club in Dalton (a nice Wayne Styles course) and Country Club of Pittsfield.
South County: Cranwell in Lenox (a Styles & Van Kleek course that was better 30 years ago prior to development around the course and the place turning into a "resort and spa"), Greenock Country Club in Lee (a Ross 9 holer built in 1927), Stockbridge Golf Club (although I have never played there I have heard many nice comments about the course) and Wyantenuck Country Club in Great Barrington (which was just discussed recently if you do a search).
Fall is a busy time to play golf around the Berkshires as many out of town folks come to see the fall foliage. I wish I knew how much history the golf scene of the Berkshires holds when I grew up there!
Have a fun time.
Ken