Appalachian Trail and US 7, Sheffield, Massachusetts The Appalachian Trail in Sheffield offers easy hikes through fields towards the Housatonic River, or forested hikes towards Egremont and Mount Everett. Northbound hikers can spot a second car at Home Road for a generally easy 4.6 mile hike—except for the last half which has some steep climbs to Home Road. The trail crosses a long trail bridge before traveling along the west bank of the Housatonic River for more than a half mile, andcontinues on a mowed path parallel to Kellogg Road before crossing Boardman Street at 3.1 miles and climbing into the forest on June Mountain, eventually reaching Home Road over occasional steep stretches. The nearby Shay’s Rebellion Battle site Monument is only a brief distance north on the Appalachian Trail from the parking area, memorializing the last battle of Shays’ Rebellion—a post-Independence uprising of farmers and war veterans against brutal economic practices.