I assisted Mike (Knotflying) with the New Bedford gathering. Pope's Island Marina is a good venue, there is a launch ramp close by, plenty of dock space, and a very accommodating staff.
I am from RI, Bristol is a very nice town, however there is limited dockage. Anchoring is good however subject to prevailing Southerly winds. Personally I wouldn't want to be on anchor for a rendezvous. We had a rendezvous in Newport RI, all activities were on the dock, luckily it did not rain. Mystic Seaport in CT is a nice place, there was a rendezvous some years ago there.
When you are planning this you need to consider dockage, a place to eat and meet onsite or at a close by restaurant. Who will you get to attend? RT/Cutwater rep? Garmin rep? local RT/Cutwater dealer etc?
Just some thoughts.