The rating of the composite at TCC does create a few issues, as it is rarely in play like that. GD rates the Clyde/Squirrel 9s, which to me is more historic...but probably does knock TCC down a notch or two because its not the current championship layout.
As for the Winchester debate, here's how this lifetime Boston-area resident lists 15 top Mass. courses (not including RI):
Essex
Myopia
TCC (composite or C/S)
Old Sandwich
Kittansett
Boston GC
Taconic
Salem
Concord
Charles River
Winchester
Eastward Ho!
Brae Burn
Longmeadow
Oyster Harbors
My next few honorable mentions: Plymouth, Tedesco (homer!), Oak Hill, Vesper (have not seen post reno/resto), Orchards
Top courses I have not seen that could affect the above list: Worcester, Sankaty, Nantucket, Hyannisport, Blue Hill, Cohasset
I would put Newport in the 4-5-6 range above, and Wannamoisett maybe half a notch lower, 5-6-7. Both are great but NCC is just more unique as a course and so important to golf as a sport.
Most puzzling to me GW-wise is the public top 10 in Mass...I've played all of them, and I have Cape Cod National as my #10 public in Mass. Come to think of it, I wouldn't mind the GW top ten too much if you just moved CCN to #10 and moved all of them up one spot.
I would love to fight with Philly golf guys about Boston's obvious golf course dominance
, but I have not played enough of their courses. I've seen the top several but not many of the #5-#15-ranked in Philly courses.