About Appalachian Trail - Railroad Street
Railroad Street in Cheshire is the crossroads of two of the most popular trails in the Berkshires--the Ashuwillticook Rail Trail and the Appalachian Trail. Cheshire, along with Dalton and North Adams are some of the very few towns where the A.T. goes through developed areas. Cheshire residents have long embraced the AT as a feature of the town center. Like the other two towns, the A.T. is also served by a BRTA bus route.
Parking for both trails is available along the Ashuwillticook Trail. Starting from the junction of the two trails, Northbound hikers proceed west on Church St, soon turning right onto School St, following the white painted blazes on the utility poles. Shortly after passing the school (now the Town offices), hikers turn left crossing an agricultural field before crossing busy Rt 8.
The northbound AT climbs briefly through another field and into the woods before emerging at the bottom of a larger field. At the top of the field, 1.2 miles from Railroad St, hikers can take a short side trip to Reynolds Rock, a large outcropping of bedrock that can be climbed for limited views (or just a great lunch spot). Continuing north, a long climb eventually brings the hiker to Noepel Shelter and Campsite at 4.9 miles, then on to Mt Greylock Summit.
Southbound from Railroad Street, the A.T. travels easterly on Main St (past Diane’s Twist Ice Cream Shop) then, crosses onto East Main St, before turning right onto Furnace Hill Road. Follow the white painted blazes on the utility poles.
At the end of Furnace Hill Road, 0.7 miles from parking, the Trail bears left and into the woods, climbing steadily to a signed short side trail to the Cobbles Overlook at 1.5 miles. The overlook offers a view of the town below, Cheshire Reservoir and a westward view of the entire Mt Greylock Range. The Trail continues south reaching the Gulf Road trailhead in Dalton at 7.7 miles.
Another approach to the Cobbles Overlook is via the Cheshire Cobbles Trailhead on Notch Road in Cheshire. The 1.7 mile trail is not marked until reaching the AT shortly before the Cobbles, but is well worn and easy to follow.
The Appalachian Trail (or A.T.), is a 2100 mile footpath stretching from Maine to Georgia. 90 miles of the Trail are in Massachusetts, traversing the Berkshires. Local volunteers manage and maintain the footpath and the surrounding trail corridor in partnership with the Massachusetts Department of Conservation and Recreation (DCR) and the National Park Service Appalachian Trail Park (NPS-APPA). While popular with both day hikers and backpackers, the A.T. is managed as a primitive backcountry trail with limited amenities. Visitors should dress for the range of expected weather, wear sturdy shoes, and carry the Ten Essentials on their hike. Bicycles and motorized vehicles are not permitted on the A.T. For more on the Appalachian Trail, visit the Appalachian Trail Conservancy’s website.