(75 miles, 3,107 ft. climbing)
A long ride 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, and through the towns of Hartland, Brownsville, and Reading. Settle in for a great ride, don't forget to stretch.
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. Route 4 bears right to go around the Village Green for a short distance to the center of Woodstock and the intersection with Route 12 (8.2 miles).
Turn left onto and follow Route 12 north through and out of Woodstock (the Woodstock Deli is on your left about two blocks north of Route 4), wind around the Rockefeller National Park past Billings Farm on the right and follow Route 12 north until you reach the "Y" intersection with Pomfret Rd. (9.2 miles).
Turn right on Pomfret Rd and follow it until Pomfret Rd. turns to the right when you reach the Teago General Store (11.2 miles). Follow Pomfret Rd. as it begins to climb, winding through incredibly beautiful hill farm country. When you reach the top of the climb (14.4 miles), shift into your big ring for a long downhill cruise. This leg starts out winding through open pasture land, and then funnels into a narrow creek side valley. Upon reaching the White River (20.4 miles), the road bends to the right, and follows the White River. This road dead ends at a stop sign (21 miles). To the left is a bridge that crosses the White River, leads to Route 14, and the West Hartford General Store.
Turn right onto the Quechee/West Hartford Rd. (unmarked) and begin to climb. At the top (24.5 miles) shift into high gear once again for a shorter downhill sprint. Keep on the lookout for a paved road on the right that intersects with the Quechee/West Hartford Rd. at a very shallow angle (26.2 miles). Carefully turn right on this road (Quechee Main St., unmarked), and almost double back in the direction you came. Follow this road through and beyond the Quechee Country Club. Go through the Taftsville covered bridge, bear left on the other side to the intersection with U.S. Route 4 (29.7 miles).
Turn left onto Route 4 east for a short distance on this narrow shouldered, highly trafficked roadway. At the intersection with Route 12 (30.2 miles), turn right. This section of road has adequate shoulders. Begin a moderate climb before it flattens a bit (32.3 miles), then you can slip into your big ring (33.3 miles) for a downhill breather before it flattens out again (35.5 miles). On your right, look for a white church steeple sticking above the treetops. The intersection with Brownsville Rd. is close by (36.5 miles).
Turn right on Brownsville Rd. This delightful, quiet country road winds around old barns, and Vermont farmhouses before beginning a bracing climb (38.5 miles) that will get your heart-rate up before leveling off a bit (39.6 miles) before dropping off into a long, brake-hand cramping downhill cruise (40.4 miles). Ski trails on Mt. Ascutney come into view before you emerge into the town of Brownsville, and the intersection with Route 44 (43.7 miles).
Turn right onto and follow Route 44 west as it winds through open farmland before ending at the intersection with Route 106 (48 miles).
Turn left onto and follow Route 106 south into the town of Reading (also called Felchville). Look for Tyson Rd. on your right (49 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 (55.1 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 (58.2 miles).
Turn right and follow Route 100 north. The road trends uphill as it winds past Echo and Amherst Lakes, into Plymouth. The Plymouth Country Store and deli is on the left (63.5 miles). Still trending uphill, following the Black River, it tops out (64.6 miles) and you begin a long downhill, passing the scenic Woodward Reservoir (65.8 miles), and winding down to the intersection with Route 4 (68.6 miles). There's a small commercial area at this intersection with two convenience stores, a deli, a restaurant, and a bicycle shop.
Turn right onto Route 4. Although this road has by far the most traffic, cyclists are blessed with extremely wide shoulders. The final leg follows the Ottauquechee River to the east back to the start at Bridgewater Corners (75 miles).