Get your way up to the Berkshires, probably means you need an escape from big city life in New York City, or from somewhere in that neck of the urban sprawl. The quickest and easiest way to get up in to the deep woods is to find yourself blazing up route 22 in NY, which straddles eastern New York State and the western border of Connecticut. Up around Millerton New York you start to get in to the real back woods. Probably has something to do with the fact that the metro north train going up there, stops in Wassaic and doesn’t go any further north, so you will notice that development, well really civilization of any sort really drops off.
Getting to the Berkshires, either Route 22 or 41 will put you in to the foothills. From there whether it’s hiking , mountain biking, any sorts of water sports, canoeing or otherwise, you can pretty much find a stop along in one of the gorgeous little towns dotted along the way which will serve as great little base camps for further adventure.