(55 miles, 1,739 ft. climbing)
This loop starts and ends at the October Country Inn. This route combines heart-rate raising climbs, cruising flats, and breezy downhills as it follows mountain valleys, alongside rushing rivers and through pastoral farmlands typical of the Vermont countryside. There are opportunities to stop for food or drink, or to use a restroom, about every 10 miles along this route.
From the October Country Inn, head west on Upper Rd. to the intersection with Bridgewater Center Rd. (.1 miles), turn left onto Bridgewater Center Rd to its intersection with U.S. Route 4 (.14 miles) and turn right.
Ride west on Route 4 enjoying a mild uphill warm-up on a generously wide shoulder. Proceed west on Route 4 past the intersection with Route 100S (5.5 miles). There is a convenience store on the left, and a country store/deli on the right. Also on the left is the First Stop Bike Shop. You will pass Killington's Skyship Base Station on the left (6.6 miles). The road opens to a flattish section through a narrow valley before it starts to climb (9.6 miles) toward the Killington access road. The steepest part of the climb tops out (10.6 miles) and then flattens a bit before a gentle climb bring you to the Killington access road (11.7miles) on the left. The Killington Deli is on the left another .02 miles to the west. Bill's Country Store is on the right.
Bear right onto Route 100N. The shoulder narrows as you begin a long winding downhill ride. You come to a brief climb into the town of Pittsfield (19.3 miles). A general store and deli is on the left (19.7 miles). Follow Route 100 N. The road flatten out a bit as it winds through a wide farmland valley.
At the intersection where Route 100 N splits off to the North (22.4 miles) bear right and follow Route 107 E as it begins to climb. This section has varying amounts of shoulder, mostly narrow, and is up and down but trends uphill as it parallels the White River to the left.
Turn right at the intersection with Route 12 S (30.7 miles). There is a convenience store on the left and the Creek House Diner on the right. Route 12 S presents a long medium grade uphill climb with a medium width shoulder. The Barnard General Store/Deli is on the left (37 miles). It has great sandwiches, and across the street picnic tables are set up on a grassy area next to Silver Lake. The climb tops out (38.5 miles) and launches into an equally long downhill glide into Woodstock (47 miles). In town, the Village Deli is on your left.
Turn right onto Route 4 W once again (47.1 miles) and follow it as it winds out of town. This final section of highway has medium width shoulders and the heaviest traffic. Fried food or ice cream is available at the White Cottage Snack Bar (48.4 miles), or deli sandwiches are available at the Woodstock Farmer's Market (48.5 miles). As you leave the town behind (50.3 miles) you begin to follow the Ottauquechee River on the left into and thru the town of Bridgewater (53.2 to 54.3 miles). Go past the Bridgewater Corners Country Store (55 miles) and turn right onto Bridgewater Center Rd. (55.16 miles), turn right onto Upper Rd. and proceed back to the October Country Inn. Put your bike in the barn, take a shower, and go across the street to the Long Trail Brewery for one of their signature brews. Sit on the deck by the river for a well-earned break.