For you folks that would rather do paved roads and still have that country feel, I recommend routes 133 and 140.
Route 140 starts off route 103 in East Wallingford, VT and ends at route 30 in Poultney, VT. Route 133 starts off route 4a in West Rutland and goes to route 30 in Pawlet. You can do these roads a a loop drive, using route 30 as a connector. I would start this loop drive at route 140 in the morning with the sun at your back. Drive it to the end at route 30 in Poultney and turn left. Drive route 30 south to Pawlet and pick up route 133 north on the left side. Drive that to the end at route 4a in West Rutland.
As an alternative ride, while driving route 30 south from Poultney to Pawlet, look for route 153 on the right. This is just south of route 149 to Granville, New York. Drive route 153 to the end at route 315. Turn left and drive route 315 to the end at route 30 and turn left. Drive north to Pawlet and look for route 133 on the right side.