Definitely check out Scarlet Hill in Groton, MA. Probably the best turnout you will find within an hour of Boston, attentive loving professional care, nice fellow boarders, vast indoor, expansive cross country course, access to miles of pretty trails, and I really liked the trainers (I worked with Meredith-- super smart, experienced, down to earth, nice, funny, normal, and will work with whatever your goals/agenda might be). Board at Scarlet Hill is $1000 plus you are required to take at least four lessons/have four training rides per month. You will easily be spending more than $1300 per month, before vet, farrier, massage, chiro, supplements, etc. For me, even as a noncompetitive pleasure rider with a 45-minute drive each way, it was totally worth it (we only left because at age 26 my horse made it known that she was no longer interested in ringwork).
Good luck, and welcome to the area!