Not sure where to put this so I guess it's General.

My Girlfriend, my dog, and my self are going to Williamstown for a long weekend.
Does anybody know of any Semi-easy riding areas? She did well at Great Brook last week but is still intimidated by the rocky-rooty stuff, and neither of us would really enjoy climbing straight up Mt. Greylock.
Anywhere around there will do (We are planning an hour's drive to Stockbridge one day) as long as it's big enough to let the dog off the leash.

All advice appreciated.