The standard approach is to buy the Goodman books, then eventually you'll get to know other backcountry skiers who will show you the real goods.
Another nice place to get some initial experience is Bryant Mtn aka the former Berkshire Snow Basin. Only 580' vert at most, and mainly low angle, but nice open terrain and relatively reliable snowpack for southern New England.
Coming up I-91, take the exit for 9W -- once you've been driving for ~25-30 min, keep a lookout on the left for a massively wide ski slope (recently cleared by DCR to provide habitat for wildlife ... like my Dynafit Snow Leopards). Drive another tenth of a mile or so and park in the cleared lot on the right. Once you're booted up, carefully cross Route 9, then skin along the snowbanks until you reach the base area.
If you ski there tomorrow, you'll see my skin track on the right (meanders a bit since I was following a boot track), although you'll also have to deal with a few tight sections up top (where the trail splits in two, and then eventually three), which I haven't cleared up yet.
If you don't ski there tomorrow, then with the rain coming in Sunday, unclear when it will be skiable again, although by then I hope to clear up the top a bit where DCR got kinda sloppy.
Also, although a summit A-frame bldg is still intact, I'd stay far away from that or any other structures -- condition could be dangerous.
The other obvious & relatively accessible spot for you is Greylock/Thunderbolt -- conditions were quite nice this morning (although of course we skied off all the freshies, sorry).