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The developing Upper Charles Trail will one day total 24 miles, linking the communities of Milford, Ashland, Sherborn, Holliston, Framingham, and Hopkinton along a former railroad bed. As of 2018, more than 13 miles of the trail are complete.
A good place to begin your trail journey is Fino Field in the town of Milford, as parking and bathrooms are available here. From Milford, the trail is shaped like a "V" with both branches paved in this community for a total of 6.5 miles. The fork heading north, past Milford Pond and Louisa Lake Park, is asphalt surfaced until it hits the Hopkinton town line. Traveling this branch of the trail offers great opportunities to view wildlife in the adjacent forests and bogs. This stretch also includes several well-marked road crossings, designed for bicycle and pedestrian crossing.
The branch heading northeast switches to a stone-dust surface at the Holliston town line, continuing for 6.7 miles to its end at the Sherborn town line. As travelers pedal through Holliston, they will encounter the historical Phipps Tunnel, constructed to allow steam trains to travel under Highland Street; the design of the tunnel, with its curved walls, is quite unique. Another highlight of this section is the Bogastow Brook Viaduct, a beautiful stone bridge with eight arches. As the trail approaches its end, you'll also traverse the scenic Dopping Brook Conservation Area. Throughout this stretch, it is clear how much the local community takes pride in the trail, from the clean and well-maintained surface to the installation of trailside art.
The trail ends on Whitney Street, with a small parking lot located at the trailhead added in 2021.
To reach the eastern trailhead parking lot in Holliston from I-495, take Exit 19 for MA 109 toward Milford/Medway. Head east on MA 109 E/Medway Road. Go 0.5 mile, then turn left onto Clark St., which becomes South St. In 1.8 miles, turn right onto MA 16 E, and go 3 miles. Turn right onto Central St. in Holliston. Here, parking is available at Blair Square off Front St. and in a municipal parking lot off Exchange St.
To reach parking at Fino Field in Milford from I-495, take Exit 20 for MA 85 toward Milford/Hopkinton. Head south on MA 85 S/Cedar St. In 0.4 mile, turn right onto Dilla St. In 0.9 mile, turn left onto Sumner St. Fino Field will come up in 0.7 mile on the left. Parking is available off Granite St.
To reach parking at Louisa Lake Park in Milford from I-495, take Exit 20 for MA 85 toward Milford/Hopkinton. Head south on MA 85 S/Cedar St. In 0.2 mile, turn right onto Dilla St. Parking is available in 0.5 mile at Louisa Lake Park off Dilla St.
To reach the western trailhead parking lot in Hopkinton–Milford from I-495, take Exit 20 for MA 85 toward Milford/Hopkinton. Head north on MA 85 N/Cedar St. In 1.5 miles, just after passing Jacob Lane to your left, turn right off MA 85 N/Cedar St. A large parking lot is located here on Cedar St. at the Hopkinton town line.
Note that the trail dead-ends on Whitney Street. There is no parking nor any way to access the trail from this northern endpoint. To ride the trail, park at any of the other trailheads, above.
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