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The Upper Charles Trail is a proposed 20-mile trail that will incorporate the communities of Milford, Ashland, Sherborn, Holliston, and Hopkinton, linking the towns via an abandoned CSX rail bed.
Milford was the first to open a complete 5.7 mile section and it extends from the town center north to the Hopkinton town line, east to the border of Holliston and south to the senior center.
From the west end of Veteran's Memorial Drive (off of Medway Road) to Mt. Pleasant Street there is a 1-mile section, known as "the missing link", which is not yet developed as a multi-use trail.

Milford Upper Charles Trail History
"build it and they will come"
by James Cockroft
Edited by Reno DeLuzio

This trail uses a rail bed that originally went through a total of six communities: Framingham, Sherborn, Holliston, Milford, Hopkinton and Ashland. Here is a picture of the type of trolley used to transport commuters as early as 1890 between Milford and Framingham on the rail bed which is now a part of the proposed Upper Charles Trail corridor: The project to convert the rail bed to the trail was originally conceived by the Conservation Commission as part of the 1993 Holliston Open Space and Recreation Plan and it was the direct result of the vision of John Thomas of Holliston. John Thomas as President of the Upper Charles Conservation, Inc. was the first to see the potential of converting the rail lines and he worked for several years gathering data and support and promoting the concept.
Read the entire story...download the PDF