Consistency is definitely the problem in New England - both in terms of wind velocity and direction. Especially during the summer. Although we sometimes do have scheduled downwind races, it's really a crap-shoot as to getting what you hoped for.
If you have a strong southerly wind: Judith Point, RI to Jamestown, RI; Woods Hole, MA to Megansett Harbor; MA, and Kittery, ME to York, ME are good possibilities. For easterly wind: Gloucester, MA to Beverly, MA.
All of the endpoints of these runs are well-protected from wind and surf, with the exception of York. These are the preferred directions, but obviously they could be run in reverse as well (although if you miss Judith Point, you'll get one shot at Block Island before eventually ending up in the Caribbean).