Wow! There is really so much to do in this great state. It's really hard to narrow it down, but I think one of my favorite places to visit is Western Massachusetts. It's often overlooked since people visit Boston or Cape Cod, but there are many attractions. The Berkshires are breathtaking with its mountains and natural scenery, and there are many cute towns that offer great restaurants, shops, and cultural attractions, such as Tanglewood, Mass MOCA, and Shakespeare summer performances. The Lenox/Stockbridge area is popular with New York tourists, but I like the bordering town of Great Barrington best. I also really love the Northampton/Amherst area. It is so vibrant with all of the colleges there, and as a result has a great cultural feel to it. There are good museums at the local colleges (UMass, Smith, Mount Holyoke, Amherst, Hampshire), great shops you can't find anywhere else (my favorite are the multiple used bookstores), and I really love the Academy of Music in Northampton-it's an old theatre where you can still see performances & movies (they do Casablanca on Valentine's Day!). Both areas also have wonderful outdoor recreation with hiking trails, camping, and lakes, as well as many family events going on every weekend, either in theatre, outdoor discovery programs, or the arts.
If people are interested, on my blog (which is pretty new, so the archive doesn't have much) I will be doing Free Fridays, highlighting free events and attractions in Massachusetts and New England for the coming weekend or month. I will try to cover different regions in the state. Check it out
http://massachusettsdream.blogspot.com/