Here's a route that has something for everyone....
Start at B&G Sporting Goods in Westfield (exit 4 off the Pike, I think) and follow route 20 up to Lee/Pittsfield. The driving/views are absolutely spectacular on that stretch of road, and the Staties are usually patrolling in Westfield. We could hit the Lee Outlet mall and then the Champion Outlet in Pittsfield if we wanted.....