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Windy, narrow, and shallow describes the river itself; as remote as one can get in the middle of Massachusetts. The Squannacook flows through Shirley as it empties into the Nashua, about 2 hours paddling from the dam, if you don't take too long exploring the pond that comes off the Squannacook. After getting on the Nashua, you'll see three obvious signs of civilization before you're done for the day - Richard's Boat House, with large dock on the water (with an incredible set of trails through Groton Place behind it), used for Groton School's crew team; the cars over the bridge of route 225 a little below there; and the new bridge of route 119 right before the takeout. The takeout is about 2 or so hours downriver from confluence of the Squannacook and Nashua, at the Petapawag boat launch. All together, it's a splendid paddle through a whole lot of conservation land - a perfect way to relax.
Spring and early summer is the time to hit this route, since the Squannacook tends to be shallow at other times, and with the fallen trees and beaver dams, can require a few haul-overs, though no true portages, unless you're paranoid about scratching up the bottom of your boat.