(18 miles, 853 ft. climbing)
A local favorite, and the October Country Inn's home route. In years past, the Green Mountain Cycling Race made three laps along this route. The route contains three legs that form an 18 mile triangular loop, with 830 feet of climbing.
From October Country Inn, head west on Upper Road to its intersection with Bridgewater Center Road (.01 miles), turn left onto Bridgewater Center Road to its intersection with U.S. Route 4 (.014 miles), turn left to the intersection with Route 100A (.03 miles). The Bridgewater Corners Country Store and deli is at the corner.
Turn right on 100A, wait for the light at the one-way bridge, and proceed along 100A. This leg of the triangular route is a generally uphill 2-lane road with little or no shoulder. The road follows small creeks as It winds between forested hills dotted with well-kept homes, and antique barns. There is little to no shoulder, but traffic is very light. After about 6 miles, you will emerge from the forrest into a clearnig where a paved entrance road to the historic Calvin Coolidge homesite angles off to the right. This is a good place to take a break. There is a restaurant, bathrooms, an old-fashioned general store, a museum, and the Frog City cheese factory at the site. Leaving the Calvin Coolidge homesite, you will descend Hysteria Hill, steep (17%) but short , to the end of 100A where you turn right at the intersection of Route 100.
This leg of the triangular route passes the Plymouth Country Store and deli is on the left. This 2-lane road is busier than 100A, and there is more shoulder. It is also more open than the first leg, following the Black River generally uphill for about 3 miles till you come to scenic Woodward Reservoir. From here its a downhill ride to the intersection with U.S. Route 4 at 13.3 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. This leg is all downhill, has by far the most traffic, but cyclists are blessed with extremely wide shoulders. The final leg follows the Ottauquechee River to the east back to a left turn onto Bridgewater Center Road, an immediate right onto Upper Road, and a short ride back to October Country Inn at 18.8 miles.
After the ride, you may want to wander across the street to the Longtrail brewery, sit on their deck alongside the Ottauquechee River, and sip one of their ice cold brews.