The Upper Charles Trail will one day span more than 20 miles, connecting the communities of Milford, Ashland, Hopkinton, Sherborn and Holliston along a former CSX rail bed. The trail is being developed in sections over two counties—Middlesex and Worcester—with the surface to be chosen by the town through which it passes.
As of 2014, the trail is open and continuous from downtown Holliston to the Hopkinton town line. About 5 miles of stone dust-surfaced trail stretches from Central Street in Holliston to South Street in Braggville. From there, the paved trail begins, stretching nearly 7 miles through Milford to the southern edge of Hopkinton along Cedar Street (State Route 85).
In Milford's town center, the trail pivots from its southwesterly course to head due north. A highlight of this segment is the trip through Louisa Lake Park, a popular spot to fish. North of Interstate 495, the trail passes through dense woodlands. The scenic and peaceful area is part of more than 1,000 acres of protected open space.
Progress continues along the Upper Charles Trail, with Hopkinton most recently opening the upgraded Center Trail on the same former rail corridor. In Holliston, the corridor north of Central Street is now owned by the town, and may be passable (but rugged) to Sherborn by intrepid hikers or mountain bikers.
In Holliston: Parking is available at Blair Square off Front Street and in a municipal parking lot off Exchange Street. On weekends only, you can also park at the New England Waterworks Association Building (125 Hopping Brook Road). On-street parking is available on Cross Street and Hopping Brook Road.
In Milford: Parking is available at Fino Field (off Granite Street) and Louisa Lake Park (off Dilla Street). A large parking lot is also located at the northern trailhead on Cedar Street (State Route 85) at the Hopkinton town line.