Upper Charles Rail Trail

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A striped header image reading "Upper Charles Rail Trail Central Massachusetts"

One of my favorite places to ride my bike in Central Massachusetts is the Upper Charles Rail Trail, which is managed in part by the Upper Charles Conservation Land Trust and winds through the towns of Milford, Hopkinton, and Holliston. Highlights of the trip include going through Phipps Hill Tunnel and over 8-Arch Bridge, along with reading about the history of the area.

A front view of a stone bridge with black, metal railings about four feet high and a dirt path over the top. A side view of a stone arch bridge topped with a black, metal railings about four feet high and a dirt path over the top. Below the bridge is rich, green vegetation. Tall trees grow in the background. A bulletin board behind a plexiglass door framed in wood. The title on the top of the board reads “Welcome to the Upper Charles Rail Trail”. Flyers advertising events and a trail map are pinned below. A view into a stone-and-brick tunnel underneath a roadway. Small trees line the steep banks near the tunnel. Stone walls line either side of the packed dirt path leading through the tunnel. Inside a brick tunnel about ten feet in height, with bright light visible at the other side. A pair of green signs with white text nailed to a wooden post declaring the rules of the path. The top sign emphasizes the importance of sharing the path, while the bottom sign reminds users to be quiet.

The Holliston portion of the trail is marked by signage covering an expansive range of topics, such as the mills and transportation of the Industrial Revolution, modern wildlife conservation, and the well-known poem “Casey at the Bat” by Ernest Lawrence Thayler. I appreciated the use of antique maps and historic photographs on the signs, as these are great comparison tools between the past and present. The research for these signs was completed by the Holliston Historical Commision, and an online version is currently under construction.

A standard interpretive sign with the title 'Welcome to East Holliston', displaying information about the area  A standard interpretive sign with the title “Casey at the Bat” including information about and photographs of baseball players from the early 20th century. A standard interpretive sign with the title 'Mudville' displaying information about and photographs of the mills in the area. A standard interpretive sign with the title 'Phipps Hill Tunnel' displaying written information about and pictures of the tunnel from the time of its construction to the present. A standard interpretive sign with the title 'Wenakeening Woods' displaying written information about the preservation area, a map of the woods, and photographs. A standard interpretive sign with the title 'Braggville' with written information about the area, a large map, and photographs from throughout the village's history A standard interpretive sign with the title '8-Arch Bridge' with written information, a blueprint of the bridge design, a map, and photographs of the bridge from its construction to the present.

The structure of the Upper Charles Rail Trail is highly accessible to people of all ages and abilities. The path is flat and straight, making it easy to traverse by foot, bike, horse, or wheelchair. The sections of the path made of compact dirt may be too bumpy for rollerblades and scooters.

The signs contain a wealth of information about Holliston. However, they have a lot of text and require some patience to read. I hope an audio version of the tour will be available in the future. Listening to the history of the area while walking or riding to to the next stop on the trail would improve the current trail experience for impatient visitors and extend the experience to the blind and visually impaired. Despite this barrier, I recommend the Upper Charles Rail Trail for anyone interested in combing local history with exercise.


Abby Epplett’s Rating System

Experience: 8/10

Accessibility: 8/10



Location: Upper Charles Rail Trail (Holliston), Massachusetts, USA