I was just in Lexington yesterday actually, Its a nice area. Very wealthy, the people in that area seem to vary from super nice to really snooty upper class. Not really my kind of area, but I still like to visit.
Theres no skiing, especially not good skiing. I would say your best bet is to hop on route 3 or I-93 and shoot up into New Hampshire. The skiing here in central/eastern Mass sucks. Wachusett Mountain is about the only place, and it might actually be faster for you to go to New Hampshire than to get on route 2 to Wachusett, plus there's better skiing up north.