I don't know anything about the CC of Pittsfield, was it well respected? I just looked in my Stiles book it was built in 1931. Taconic I would think should be included. As far The Orchards, I've exclued nine hole courses in the past, but I might make an exception for Mass. I think there were a few interesting nine-holers.
Brookline - 1894 W.Campbell, ? A.Campbell, 1913 Windeler
Essex County - 1894 W.Cambell, 1907 Willett/Caner/Dunn/Travis, 1911-1917 Ross
Salem - 1925 Ross
Charles River - 1921 Ross
Myopia Hunt - 1894 W.Campbell, ? Leeds
Brae Burn - 1912 Ross
Vesper - 1895 ?, 1899 Findlay, 1919 Ross
Belmont Springs - 1909 Ross
Winchester - 1902 Findlay, 1916 Ross
Oyster Harbors - 1927 Ross
Berkshire Hills - 1926 Tillinghast
Eastward Ho! - 1922 Fowler
Sankaty Head - 1921 H. Emerson Strong
Longmeadow CC - 1921 Ross
Dedham Country and Polo - ? Ross, ? Raynor
Kittansett - 1922 Wilson/Flynn/Hood
Taconic - 1896 ?, 1927 Stiles