(44 miles, 1,906 ft. climbing)
A ride of intermediate length that starts and ends at the Bridgewater Country Store, close to October Country Inn. This route goes through the town of Bridgewater, and brushes by the village of Woodstock, the "prettiest town in New England' before heading into the verdant Vermont countryside. There are five legs, of more or less equal parts uphill-for almost 2,000 feet of climbing-and downhill, on this 44 mile route. You might even see a moose.
This route starts in Bridgewater Corners at the intersection of U.S. Route 4 and Route 100A. Head east on Route 4. This is the most trafficked section. Shoulders are adequate. You soon come to the town of Bridgewater (1.6 miles). Upon leaving, the road winds alongside the Outtaquechee River into Woodstock. The intersection with Route 106 (8.0 miles) is on the right as Route 4 bears right to go around the Village Green.
Turn right on Route 106 and peddle south. On narrow shoulders, this less traveled road trends uphill, passes the South Woodstock Country Store (12.8 miles) winds through horse country before it start climbing (14.3 miles) increasing in pitch until it tops out (15.8 miles) and drops into a long downhill, past the intersection with Route 44 (20.8 miles), into the town of Reading (also called Felchville). Look for Tyson Rd. on your right (21.8 miles) between the post office and Shaughnessy's Reading Country Store.
Turn right on Tyson Rd. This narrow quiet shaded country road has no marked shoulder, but there is little traffic. This is a long climb of varying pitch, but drop it into your small ring, take your time and enjoy the ambiance. Near the top, moose are often seen hanging out in the marshy area. After the summit (27.9 miles) slip into the big ring. With the exception of one small up and down section by Colby Pond, the rest of the ride is a peddle free downhill ride on a winding paved road through shaded forest and open meadow until you reach the junction with Route 100 (31.6 miles).
Turn right and follow Route 100 north. The road trends uphill as it winds past Echo and Amherst Lakes, into Plymouth, and the junction with Route 100A (36.7 miles).
Turn right on Route 100A, you're immediately faced with a very steep but short uphill that tops out (37.2 miles) into a long downhill. Plymouth Notch (37.6 miles), a historic site marking the birthplace and home of Calvin Coolidge. A short bypass to the left takes you to a General Store, and a restaurant. This quiet stretch of downhill road winds through a forested valley ending this loop at the intersection of Route 4 (43.7 miles).