When you find what you are looking for and it’s affordable and has good turnout, please let me know.
I grew up in this area, moved to RI, then spent a few years in SC, then spent a few years in NY, and then finally moved back to MA just before hitting my 30s. It is expensive!
The pros about this area: it has a lot of very talented dressage trainers, there’s a good scene for shows (both recognized and schooling) and the quality of horses is top notch.
The cons are that there is a dearth of land, schoolmasters, real estate, and traffic free roads… which drives up the cost[s] of pretty much everything horsey here.
A caveat is not to trust what google Maps or any map feature says about traffic times/commute times. Generally anything in that area is always awful around rush hour and it may take you 45m to go 8 miles.
Last time I shopped in your area for board it was closer to the $1500 mark and even then the horses only saw a few hours of turnout a day. I’ve been looking for a few years now for a place to winter-board just to keep my guy going, but always end up just giving him the winter off.
If you can afford it it may be better to just outright buy a home – but even then, real estate taxes approach what you pay in a top quality show barn annually, so it really depends on where you see yourself in a few years… If you’re thinking your presence here is a permanent fixture, it may be better to buy - but it sure is expensive.
I would join this FB group and ask:
https://www.facebook.com/USDFRegion8