Hi Chris, I have been on US 20 from Springfield to Sturbridge and it is the easiest way between the Ct. valley and the Quinnebaug, It's only sketchy going through commercial centers, there is a trail that starts in Brimfield and runs to Sturbridge from there I follow the river down to the Airline north and go east to Ma or west to Willimantic. The trails of Eastern Ct.are mostly dirt pretty smooth except for the northern sections above Rt6 you need knobby tires Airline north connects to the SNETT and goes to Blackstone Ma and then across the river it goes east to Franklin Ma. The Airline south from Willimantic to Portland Ct, is smooth dirt except for a few miles around Willimantic that are paved, The way I go from Hartford east is the Charter Oak Greenway(paved) to the Hop River trail down to Willimantic where you can start going NE or SW on the Airline.Crossing the ridges on 6 all the way to Providence is a *****. I just did it Thursday. Most of the easy routes are the US numbered, the smaller roads have less traffic and bigger hills. If you wanted to connect to the coast from Willimantic you can go down Ct 32S to Ct 207E to 138E and into RI or go south Ct 49 to Stonington/ Westerly not bad hills.