JHern, is your base going to be in MA or NH?
New Hampshire is a bit of a DG desert. There's 0 public courses but I've heard only good things about some the pay courses (Beauty Hill, Terrence Pines).
If you're based in western MA...
Detour a couple hours to Worcester and go play Maple Hill. The Pyramid's pro shop (AKA Marshall Street) is something special also (as is the Pyramid's course, natch).
Buffumville Dam is another good course with 27 holes.
If you're willing to trek across state (maybe 2-3 hours from springfield), Borderland State Park in Easton MA is (IMHO) the best course in New England. 18 holes (two tees & two baskets each hole) that wind around and near a beautiful 19th century mansion. Yes, that means FOUR layouts (not sure if anyone's ever played all 4 in one day? I wouldn't recommend that
A few hours south would get you to Wickham Park in Hartford CT. The reviews speak for themselves.
Another epic course is North Calais, VT. However, it is open only two weeks a year (early august) and only to players signed up for the VT states.
I should mention that MH & Pyramids are both $5 a day.
Check out NEFA.com for more info