Do yourself a favor, when you get into the CT-MA area buy a RUBEL "Western Mass" bike map. Should be available in Salisbury CT, at "The Village Store" bike shop, 19 Main St, (Rtes 41 & 44) 860-435-9459, or in Great Barrington at one of two bike shops. "Harlan B. Foster", 15 Bridge St, 413-528-0564, or "Berkshire Bike & Blade", 326 Stockbridge Rd, 413-528-5555.
These maps have excellent info for bicycling, shows the ups & downs for the terrain, and has recommended and secondary routes to use.
From Great Barrington to Stockbridge to Pittsfield, the map shows two alternate routes besides RT 7, and north of Pittsfield, RT 7 has a good shoulder.
After you do your ride from NJ this coming weekend, would you either post the routes you took, or send me a PM or e-mail. I'd be interested on how you went after you crossed the river into Poughkeepsie (SP-?) to Millerton to Salisbury to GB.