Chalet WMA Massachusetts Division of Fisheries & Wildlife Cheshire Cobble Trailhead
Notch Road, Cheshire, MA

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Cheshire Cobble Trailhead in Cheshire, MA | Berkshires Outside
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About Cheshire Cobble Trailhead

This is the parking area for the Cobbles Trail, a short, steep hiking trail in Chalet Wildlife Management Area. The path is only 1.7 miles but has a high reward with expansive scenic views from Cheshire Cobble. Visitors will enter a quiet forest and climb steadily toward the Appalachian Trail. This trail, a 2,000+ mile recreation pathway from Georgia to Maine, travels throughout the Berkshires. Going northward on the Appalachian Trail, visitors will arrive in downtown Cheshire and eventually at the summit of Mount Greylock. Regardless, for the overlook, hikers should continue southbound. The trail will gradually get rockier as it climbs. Then, it will open onto a scenic outlook toward the west. Visitors can see the Town of Cheshire, Mount Greylock, and other picturesque mountains in the distance. When the weather cools, this area bursts with the yellows and oranges of fall colors.

Wildlife viewing is excellent in this Western Massachusetts forest. In addition to birds, plenty of other animal species—including moose—live in Chalet WMA. The area is also great for hunting. Bear, turkey, white-tailed deer, and other game species thrive in these undeveloped woods.

Parking for this area of Chalet WMA is off Notch Road, just after it splits with Windsor Road. Additional parking is also at the Ashuwillticook Trailhead in downtown Cheshire.

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Notch Road, Cheshire, MA

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Looking to meet up with others for team sports or group activities? Check out our list of clubs and leagues in the Berkshires. We also link to an array of outdoor recreation resources: retail shops for gear, rental facilities for equipment, and guides to get you where you want to go! Our list of summer camps will help you plan an overnight or day camp adventure for your young ones.