The trail starts along the future extension of the Upper Charles River Reservation trail at the Mary Hunnewell Fyffe Footbridge located near the intersection of I-95/Rt-128 and Rt-16 in Newton.
For the first 7 miles the Charles River Link is part of the Wellesley Trails network. It follows the Charles River Path along the river, through the Wellesley Town Forest, and past Longfellow Pond. When reaching the Sudbury Aqueduct, it follows the Sudbury Path along the aqueduct through Babson and Olin Colleges to the Waban Arches. It then connects to the Guernsey Path, which runs along the Charles River to the Needham town line.
In Needham the Charles River Link crosses the Charles into Dover at the Charles River Street bridge. It follows roads to Pegan Lane and takes trails in Pegan Hill Reservation where there are views of Nobscot Hill, Mt. Wachusett, and Mt. Monadnock. After taking a trail through Mumford Wildlife Forest, it takes roads to Glen Street and follows trails through Peters Reservation to the Charles River.
The trail continues through Chase Woodlands and follows roads to the Dover-Sherborn Regional High School. It enters the Medfield State Forest in back of the school and takes trails to and along the Charles River to a steep bluff overlooking Rocky Narrows, known as the "Gates of the Charles."Then the trail continues along the Charles River in Medfield to the Charles River Gateway overlook at the Medfield State Hospital, runs along an old woods road, and ends at Hospital Road where it intersects with the Bay Circuit Trail.