Greylock can be climbed when there isn't snow/ice, the road is gated during the winter months but nothing is really preventing you from riding it if it is ice free. There are decent climbs on the MA/NY border over the taconic range and some nice flat rides in the area for times when not interested in climbs. The Catskills are an hour to 2 hours away, the high peaks of the Adirondacks are about 2.5 hours away, Lake geoge climbs are closer. The Whites are around 3.5-4.5 hours away, all those points offer more ascents.

Ascutney is about 2 hours away, it offers a mtn that has a road. Equinox Mt, by Manchester is about 1 hour away, another mtn with a road on it.

The berkshires itself will present you with rolling hills, nothing too crazy. Williams college will put you closer to NY and the catskills/ADKs and Amherst will put you closer to the Whites.. Amherst itself is in a vallley and there are hills there (holyoke range, mt Tom.. and you'll be close to Wachusett (road).)...

Jay