Something we very much enjoy about living in the Hilltowns is our dirt roads. These old and usually historic means of getting from town to town were how the early settlers got around…sometimes referred to as cart road, goat path, the old road to whichever town you needed to get to. These roads make for great hiking especially when the weather is not so appealing! Look out for mounds usually with large old growth trees in front of it or a particularly flat section of road lined on both sides with giant trees and you will find the cellar holes. Old water troughs can be found too. GAIA has an 1800 and 1900’s layer that shows them all!
Historic Round Hill Road in Chester, road to Blandford has cellar holes, two cemeteries and you definitely don’t drive it in winter. An unexpected small cellar hole Russ and I found.