I present to you <a href="http://www.mapmyrun.com/run/united-states/vt/killington/1082223451" target="_blank">The Killlington Killer</a>, a monstrous half-marathon loop.<br><br>
Two solo laps of this beast would be a major accomplishment. This will be great training for Pittsfield. Total elevation gain and loss is about 1000' per lap, primarily gained and lost in one single withering climb and one punishing descent. Even better, and probably safer because of the size of Rt. 100, would be to run the heart of this loop, miles 6-12, as a double out and back. This would double the elevation figures and keep you off of Rt. 100.<br><br>
The Mountain Road is tight and twisty, and very steep, at the south end, and commercially developed at the north end. Two shortcuts can tighten the loop to about ten miles. Rt 100 is a major road. It should have a very broad shoulder, but expect downshifting trucks.<br><br>
Otherwise, feel free to explore the minor roads with MapMyRun.com or G-MapsPedometer.com.
