Pittsfield was the first town to pop into my head.
Back in 1962 on the way to climbing Mt. Greylock, I was tracking elevations using a barometer which also had (quite conveniently) a "feet above sea level" scale. You set it at your start, knowing its elevation.
Once up the big hill on Rte. 7 just north of Stockbridge, it hit 1000 feet and stayed around there all the way through Pittsfield and on to the start of the Cheshire Harbor Trail.
BTW, I'm pretty sure Peru, MA, in Berkshire County is one of the, if not the, highest incorporated communities in New England. It's a fun place to visit, having a very different, Edward Hopperish feel to it.
Why did I climb the mountain? Because I was there.