The Chester-Cambridgeport Loop is a 26-mile ride with a moderate rating
Travel through picturesque historic towns beginning at the Green on Main Street in Chester and continuing straight onto Vt. Rt. 103 South for approximately 6 miles before turning south onto Pleasant Valley Road.  The trail bears right at the intersection with Vt. Rt. 121 and follows a narrow,winding, yet fairly flat  stretch to the town of Grafton.  The trail then turns right onto Vt. Rt. 35 North, which has some steep hills -- both up and down -- traveling back to Chester. Turn left at Chester Hardware to return to the Green.

Please think safety first when bicycling Vermont's scenic roadways, many of which are winding. Wear a helmet and beware of motor vehicles. On our unpaved roads, please know that besides being winding, many are quite bumpy and logging trucks are common.

The Vermont Recreation Directory