Round Top Hill is the highest peak in Hampden County at 1,780 feet and is the fifth highest peak in Massachusetts. This property off Round Hill Road in Chester, MA was permanently protected in 2015 through a Conservation Restriction held by Hilltown Land Trust.
The land remains in private ownership, but the landowners allow the public to hike the trails to the summit of Round Top Hill. Please respect the property and stay on the trails.
When the leaves are down, hikers have a 360-degree view of Hampden County. Some notable views are the white church in Blandford, Gobble Mountain in Chester, Chester-Blandford State Forest, Beckett Quarry, and sometimes as far east as Mount Tom in Holyoke. Atop the summit there is a unique ecological environment of grassy open areas with scrub oak and shagbark hickory trees.
Hiking Round Top Hill
There are two trails to the summit of Round Top Hill, both leaving from the west side of Round Hill Road.
The orange-blazed Round Hill Trail is a moderate-to-steep wooded trail, with one steep section of rock hopping. The trail is .5 miles to the summit. The Round Hill Trail is labeled “Fire Road” on the map below.
The white-blazed section of Unkamit’s Path that leads to Round Top Hill is an even steeper and more challenging approach to the summit, including several steep ledges. The trail is .4 miles over rugged terrain. Western Mass Hilltown Hikers help maintain this trail for the public.
Parking & Directions
To get to both trailheads, take Route 20 or Route 23 to Blandford Road in Chester then turn onto Round Hill Road which is at the Blandford-Chester Town line. Follow Round Hill Road until you reach an overgrown logging landing on the west (left) side of the road. There is a sign on the road barrier indicating the distance to a trail uphill. This is the Round Hill Trail marked with orange blazes and a metal sign. Be warned there is no formal parking area, only a small pull off, and the trail is not regularly maintained by the property owners.
The section of Unkamit’s Path which is white-blazed is located a short way north of the junction of Round Hill Rd and Griffin Brook Rd. Park at the State Park area a short way down Griffin Brook Rd. Walk back to Round Hill Rd. and walk to the right a short way to a white blaze and metal sign on the left side.
NOTE: The upper portion of Round Hill Road is not maintained by the town of Chester from November 1 to April 15. During this time of year the only way to access these trails is by parking at the cemetery and walk into Round Hill Road.