Mount Greylock State Reservation Massachusetts Department of Conservation and Recreation Round Rocks Trailhead

Rockwell Road, Cheshire, MA

About Round Rocks Trailhead

The Rounds Rock Trailhead brings visitors to an expansive hiking area in Mount Greylock State Reservation. The Rounds Rock Trail is an easy hiking trail with excellent scenic views of Western Massachusetts. The path leaves from across Rockwell Road and climbs gradually up a rocky slope. After traveling through a dense hardwood forest, visitors will arrive at rocky outcroppings with low bushes. These bushes become covered with fresh huckleberries in late July.

While walking along these rocky outcroppings, visitors will see a pathway branch to the left. Visitors can follow this branching trail and access a beautiful overlook of the Berkshires toward the south, perfect for a short pitstop or a long picnic. Further down the path, another small track will branch toward a picturesque overlook.

After the overlooks, the Rounds Rock Trail will loop back through a hardwood forest toward the trailhead. Near the far end of the loop, visitors will see the site of an old plane crash.

Meanwhile, the Woodason Spring Trail, which leaves directly from the parking lot, takes hikers north toward the Jones Nose Trailhead or south to the Visitor Center.

There is a designated parking area along the shoulder of Rockwell Road. When Rockwell Road is closed between late October and mid-May, this trailhead is only accessible on foot or snowmobile.

The State Reservation is open for hunting from Columbus Day to May 19th; however, it is prohibited within the Summit's War Memorial Park any time of the year.