We took our closest friends (3 couples) to a very "fancy" restaurant in Boston. The dinner and service was great, but not overbearing. My only regret is that it was about 6 months before we met our cycling friends.
We also went for a weekend in Portland, Maine. We took the train there early on Saturday and spent the day walking and eating. It was eerily warm for the beginning of October; I remember eating outside at lunch. I think I had a massage at the hotel and we used the gym there. We left after brunch on Sunday. Short, but fun.