Thanks Todd. That's a new one for me. I posted this question on Team Titleist and got some good responses. I figured I would share this for all the other Massholes out there.
Shaker Hills, Harvard, MA (always a local favorite and ranked high)
Red Tail Golf Club, Devens/Ayer, MA (very nice but too pricey IMO, worth playing though every so often but I usually play during edge season rates)
Meadow Creek, Dracut, MA (Good conditions and overall nice track)
Butter Brook, Westford, MA (played a couple times and liked it)
Trull Brook, Tewksbury, MA (some odd 90 degree dogleg holes but overall a nice place to play)
Cyprian Keyes GC, West Boylston, MA (My 'home club' - about 50 minutes from you, good conditions, TOUGH layout that makes you place the ball, only hit driver a few times a round if you want to score)
The Pinehills, Plymouth, MA (always rated well, 2 courses worth playing)
Crosswinds Golf Club, Plymouth, MA (great value, cheaper than others in that area and good conditions)
Sagamore Springs, Lynnefiled, MA (haven't played in a LONG time, but I recall as being decent and it is close to you)
Gannon Municipal, Lynn, MA (haven't played in a long time, good course though and has a view of Boston)
The Meadow, Peobody, MA (have not actually played but heard good things - they held a qualifier for one of the MGA tourneys last year or the year before.)
Shining Rock, Northbridge, MA (just started playing here....newer course, GREAT greens, good value for $)
Highfields, Grafton, MA (can be tough to get out weekend mornings due to blocked times for inner club members)
Campbells Scottish Highlands, Salem, MA (I played in a league here for a few years, pretty good conditions and you can go low)
Beverly Golf and Tennis, Beverly MA (reasonable prices and a good layout, hosts the High School Championships)