[NOTE: we've split this discussion from a topic that was started on the Boston board at http://www.chowhound.com/topics/show/... - The Chowhound Team]
You did say Massachusetts!
My most memorable dining experience in Massachusetts - food, wine, setting, and service was at Toppers at the Wauwinet on Nantucket. I think my husband would agree.
It has been a few years but our time there was so perfect that we arranged a repeat of the experience for friends as their wedding gift from us. (They were on a sailing honeymoon that included a stop on Nantucket.)
They actually called us from the beach in front of the Inn to tell us it was their best wedding gift and that they would always remember this meal as a highlight of their honeymoon. They still talk about it and thank us- years later.
If you ever go, be sure you take advantage of the wonderful boat ride to and from dinner that they offer as a part of their service.
Thank you for making me remember this. I'm going to make plans to go back.