(35 miles, 1,470 ft. climbing)
A good medium length ride on a Summer day. Starts and ends close to Woodstock. Wanders along two-lane roads through several small Vermont towns, open fields, farmland, and forest. The ever present ponds, rivers, streams, or creeks are never far away. This ride can be increased to 53 miles when combined with an out-and-back from the October Country Inn.
Park in the Billings Farm overflow parking lot. Leaving the parking lot, turn left onto and follow River Rd. This lightly trafficked road soon turns to hard-pack dirt (0.7 miles). Bear to the right at the "Y" intersection with High Pasture Rd. (1.5 miles). Follow River Rd. alongside the Ottauquechee River to its end at the intersection with Quechee Main St. (2.9 miles).
Turn right, and go through the Taftsville covered bridge, bear left on the other side to the intersection with U.S. Route 4 (3.0 miles).
Turn left onto Route 4 East for a short distance on this narrow shouldered, highly trafficked roadway.
At the intersection with Route 12 (3.5 miles), turn right. This section of road has adequate shoulders. Begin a moderate climb before it flattens a bit (5.6 miles), then you can slip into your big ring (6.6 miles) for a downhill breather before it flattens out again (8.8 miles). On your right, look for a white church steeple sticking above the treetops. The intersection with Brownsville Rd. is close by (9.8 miles).
Turn right on Brownsville Rd. This delightful, quiet country road winds around old barns, and Vermont farmhouses before beginning a bracing climb (11.8 miles) that will get your heart-rate up before leveling off a bit (12.9 miles) before dropping off into a long, brake-hand cramping downhill cruise (13.7 miles). Ski trails on Mt. Ascutney come into view before you emerge into the town of Brownsville, and the intersection with Route 44 (17 miles).
Turn right onto and follow Route 44 West as it winds through open farmland before ending at the intersection with Route 106 (21.3 miles).
Turn right onto and follow Route 106 North as you begin a long moderate climb along this forest ringed roadway until it kicks up with earners (25.6 miles) until to go over the top (26.3 miles) and get a downhill break through horse country. You will enter the town of South Woodstock. The General Store and deli is on the left (29.2). Continue north on Route 106 until it ends at the intersection with Route 4 in the town of Woodstock (34 miles).
Turn right onto Route 4 for a short distance to the center of Woodstock and the intersection with Route 12 (34.2 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 to Billings Farm and the intersection with River Rd. (34.7 miles).