These are mostly third party reccos, so consider the following as research fodder rather than valuable tippage. Any comments, negative or positive, welcome, as well as additions to the list (let's make a monster resource!)
Roadside Store (935 Main Rd Monterey, MA (413) 528-2633), open seven days a week from 7:30 to 2:30, is 8 miles east of Great Barrington, on Route 23 in Monterey and associated with Gould Farm (100 Gould Rd Monterey, MA (413) 528-1804) and I have friends who consider this the best breakfast in America.
Claremont Cafe on Columbus Avenue near Mass Av in Boston is supposed to have great huge scones. Another boston breakfast tip: Charlie's on Columbus Ave. in the South End
Miss Adams Diner, Rt. 8 south, Adams, MA 743-5300 (no, not a beauty contest winner, it's really a diner)
miss florence diner in Florence Mass near northampton (good for grasshopper pie)
Blue Bonnet Diner King st. northampton for breakfast
I'm not sure where Chatham, MASS is, but I have this tip on file: Old Harbor Bakery and Coffee Shop, 95 Old Harbor road, Chatham, MA, 508-945-4380
Lloyd's Diner (Framingham,MA., 1940's Worcester) "Huge great breakfast"
I found the following in my notes, and am not sure what to make of it (I didn't write it...it's a clipping from somewhere...so caveat eater):
SoundBites: Now here's a concept: buttery but not greasy breakfast. SoundBites may be a little out of the way for your day's start, but the restaurant serves up as delicious and fresh an omelet as you're likely to find. The mashed home fries, Wonder Waffles, and serve-yourself coffee are so good that they take the guilt out of loading all your calories and caffeine into the morning hours. 708 Broadway, Somerville, 617-623-8338.