The Cheshire Trail parking spots are at Joslin Station Road, Mount Huggins Road, and Webb Depot Road. The Trail begins in Swanzey at the north Joslin Station Road, 0.2 miles south of State Route 101 near the historic old stone bridges over the Branch river. Going south the trail goes past homes, through forests, past the Cheshire Fairgrounds, and through several impressive deep stone grades cuts. At the south end the trail passes from Swanzey into Marlborough, and passes over a second old historic stone bridge at Webb Depot Road. This section of the trail is 4.2 miles in length.
The Ashuelot Trail runs parallel to the Cheshire Trail, on the west side of Swanzey. The trail crosses the town line near the Krif Road in Keene, at the entrance to the Keene State College Athletic Complex. Parking is available at the end of Krif Road. The trail then runs southwest through forests, over an old railroad bridge, and passes over Sawyers Crossing Road near a second parking area. The trail then continues southward through West Swanzey, past farms and fields, and runs along the Ashuelot River until it reaches the Winchester Line. This stretch of the trail measures 7.2 miles.
