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By Sharon O'Conner owner, Backroad Discovery
Starting at the Mill Tavern in centrally located Londonderry, take route 11 east (7.5 miles) to Hill Top road on the left. Shortly (1.3 miles) you meet the Weston/Andover road; take a sharp left for half mile, then go right up Hill Road which becomes a dirt road running along a ridge with vistas (including Magic Mtn. ski area) and farms. After 3 miles on Hill turn right on Lovejoy Brook Road for a steep one lane dirt road down the mountain crisscrossing a stream in thick woods.
Lovejoy ends after 3 miles at Smokeshire road. Go right and continue about 4 miles on this beautiful dirt road that parallels the Williams River with its multi-colored rocks indicating the different minerals including gold that are in it.
Continue on into Chester (passing the Chester Station on the 26 mile scenic railroad). Relax in Chester with its beautiful main street. Have a bite to eat (outdoor dining) at Raspberries & Thyme. Visit the National Survey Company Charthouse that publishes many of the maps in America. Explore the Hugging Bear Inn & Shoppe.
Continuing on Houghtonville for about 5 minutes, you enter the 1800s and tiny Grafton, a former sheep farming village that has been transformed with the support of the Windham Foundation into almost a living museum. For instance, Grafton Cheese Works still makes cheese mainly by hand. Park near the "The Old Tavern" - 200 years old in fact. See why Rudyard Kipling (yes, the jungle books were written in Vermont), Teddy Roosevelt, Henry David Thoreau and others vacationed in Grafton. Have a root beer on the village store porch. Explore.
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When Smokeshire ends at VT 103, turn right and go a quick 5 miles to the outskirts of Chester then slow down and look for Stone Village which consists of about 10 or more stone (mica schist quarried locally) houses - some say the only such grouping in the US. The homes, private now, were built in early 1800s. Further down the road half a mile on the left is the Yosemite Fire House with its unique towers to dry the fire hoses.
Leaving Chester on Route 35 South, go 2.5 miles then turn right after a bridge on Popple Dungeon Road then (after 1 mile) take Stage Road on the left. Try to image a stage 150 years ago going up the hill you will be taking! After about 1.5 miles, a left fork leads fifty yards to the quaint Cobb cemetery with its old Vermont names and dates. Backtrack to Stage Road to continue to Houghtonville Road. Make a left noting the red brick house of Oliver Davis who fathered 17 children with 2 wives!
It is time now to leave the early 1800s so take VT 121West from Grafton for about 9 miles then go left on route 11 for 5 miles back to the Mill Tavern in Londonderry. Under 50 miles total trip.