Good company. Pittsfield is what it is.... Here are a few suggestions for places to check out as that area is where I grew up.
Go to Bolley's hot dogs in Waterville--two dogs loaded, large frie, large choc. Speak and move swiftly down the line. You will not be dissappointed. Keep tums available.
"Big G's deli" in Winslow. The biggest bestest cookieen sammiches evar.
Check out a funky store called "Sign of the Sun" downtown waterville. Kind of a indian/hippie place, with jewelry, vinal and cool posters.
Sonny's Pizza in Fairfield is kind of a local icon--been there forever.
Other than that, you're screwed. Oh, with your job in Pittsfield, I think I would try to live close to Fairfield. Cheap rent, close to Waterville and you jump on the highway and 15 minutes to Pittsfield.
My .2
Jeff?
My $0.02?
Bolley's - Gone WAY downhill since the old days. Last time I was there, the cook had a cigarette in his mouth. And even as a smoker, I was still disgusted. Haven't been in years since that incident. Hell, don't even know if they're still open.
Big G's - FTMFW, that is all. Maybe I'll take Run after his first day.
Sign of the Sun - Not my thing, but definitely Run's.
Sonny's - A resounding meh. Never figured out why everybody raves about this place. It's not bad, just generic. And it's got nothing on Korner Store in Oakland. Best pizza anywhere.
And I'd like to add:
T&G's Smokehouse - Best BBQ anywhere, period. It's just a little cart in the Aubachon's parking lot in Waterville during the summer months, but it's amazing.
The Early Bird - Best homemade breakfast in the area. Sausage & cheddar omlette w/ Texas toast, yummy.
Noteable mention - The little chinese place across from Cianbro corp. office in Pittsfield. It's not the best, but the best place to get food in Pittsfield. Also heard Cervasa's mexican in Newport aint bad either.
As for places to live, I'm rather partial to Oakland, but it tends to be a bit pricey compaired to the rest of the area. Winslow's not bad either. Near town but still kinda out of town, like Oakland.