Map of the Upper Charles Rail Trail


Upper Charles Trail

Upper Charles Trail Massachusets map area

Upper Charles Trail


11 miles


paved / graded crushed stone


Milford, Holliston


rail-trail, historic bridges, forest


Regional Trails

The Upper Charles Trail is a proposed 25-mile long system of trails that is located in the communities of Milford, Ashland, Sherborn, Holliston and Hopkintown in Southeastern Massachusetts. Portions of the trail have been constructed. The town of Milford has constructed 6.25 miles of paved pathway that extend to the north and to the east from the middle of Milford. Beyond the town limits of Milford, the trail is improved in sections, but not entirely paved. This 4.75 mile section travels through Holliston.


The Upper Charles Rail Trail has paved and unpaved sections. The trail is open for non-motorized use such as bike riding, walking and running. There are a few street crossings, but the trail travels away from traffic.

The Upper Charles Trail is in various states of improvement. All of the 6.5 miles of trail in Milford is paved. At the Milford/Holliston town boundary the pavement transitions to stone dust to an area east of Hopping Brook Road, approximately  one mile. The trail northeasterly is unimproved gravel or temporary gravel and is suitable for mountain bike for another mile until reaching Summer Street. Stone dust starts again and runs for 1.5 miles to the center of Holliston. Beyond the center of Holliston the trail is not open and is course railroad ballast, suitable only for walking.

Points of Interest
Milford Pond
Fino Field
Plains Mall
Weston Pond Recreation Area
Wenakeening Woods
Lake Winthrop
Robert Adams Middle School
End Points

The 4.2-mile long west branch of the paved Upper Charles Trail starts at a trailhead located along the east side of Cedar Street, 0.5 miles north of Walden Way. This branch of the trail stops at the Milford Senior Center on N. Bow Street in the middle of Milford.

The east branch, which is also paved at this point, starts on Mt. Pleasant Street, just south of Beach Street in the middle of Milford. The trail is paved as far as Zain Circle. To the northeast, the trail has a surface of compacted crushed stone or a natural surface. This section ends at Whitney Street in Sherborn.


Following are links to official off-site resources to find out more details about the Upper Charles Rail Trail, Massachusetts.