This town sits at Northbound AT mile 1580, Southbound AT mile 612 and has approximately 3,142 permanent residents.
You can get there by taking Interstate 90 from the East or West, exiting on Route 7 in Lee, MA. Then drive North on 7 until you enter Pittsfield. You can take a right on Route 9 or a right on Tyler street and follow this until it intersects with Route 8, at which time you will go North towards Cheshire. The AT crosses Route 8 at the far side of town. As soon as you pass Harry’s Auto Sales on the left, you will see a small sign for the AT on the back of a street sign. Look also for the white trail markers on either side of the road.
In Cheshire, you will find a post office, a few small places to get groceries including a farm market, a Dunkin’ Donuts; Diane’s Twist – a great place to get ice cream in the summer; and The Bass Water Grill – serving dinner only. There are not many lodging options in Cheshire, with the exception of the Harbour House B & B, which offers 6 rooms and breakfast for a moderate price. Otherwise, there are on-trail camping areas not far from town and the beautiful Bascom Lodge atop Mount Greylock (see Hike section). Since the hike is a doable drive from our home, we did not stay in town.
Chesire, MA is located in the Hoosic River Valley, and is the site of a dammed reservoir on the river. To the west, parts of Mount Greylock State Reservation make up part of the town and includes a section of the auto road. To the southeast, North Mountain peaks just outside town limits before descending into the valley. The Appalachian Trail crosses through the center of town, heading from North Mountain to Mount Greylock. The Southern foothills of the Hoosac Range make up much of the Eastern side of town. The land is dotted with sections of the Chalet and Stafford Hill Wildlife Management Areas. Albany, NY is home to the closest airport and Springfield, MA has the closest major bus terminal.
One of the newest towns added as an A.T. Community in 2018, Cheshire has long been a hiker–friendly town. Serving as a central location for all kinds of A.T. hikers as well as cycling and walking on the 11 mile Ashuwillticook Rail Trail, connecting the Berkshire towns of Lanesborough, Cheshire, and Adams. Cheshire Lake is another recreation resource for kayaking, canoeing, paddleboard, swimming, fishing, and boating. In the winter the Ice Fishing Derby is also a popular event.
Cheshire is a starting point for A.T. day hike destinations. The Cobbles (1.1 miles south) is a vista with sweeping views of Mt Greylock, Cheshire Lake, the town and surrounding countryside. A similar distance north, an open farm field offers views east, and a 30ft. high glacial erratic, Reynolds Rock. The town also serves as a starting location with ample parking for more ambitious hikes to the summit of Mt Greylock, 7.7 miles north on the A.T.
For further info., contact the New England Regional Office of the Appalachian Trail Conservancy at 413-528-8002; the AMC Berkshire Chapter Facebook page, https://m.facebook.com/Appalachian-Mountain-Club-Berkshire-Chapter-173257052722077/; or the Cheshire Appalachian Trail Community Facebook page, https://m.facebook.com/pages/category/Community-Organization/Cheshire-Appalachian-Trail-Community-103005510488957/#
