If you’re looking for a unique hike in Massachusetts, this is it. Upper Charles Trail is a rail trail that features beautiful natural sights, easy terrain, and a gorgeous old train tunnel. Here’s everything you need to know about tackling this charming trail.

TripAdvisor/ Emmalach
The Upper Charles Trail in Holliston is a treat for the feet and eyes. Walkers and cyclists will love this 12.3-mile trail that meanders through small towns in Middlesex and Worcester counties. The trail is built over former railroad tracks, so you’ll be exploring along the path of the Bay State’s oldest rail route.
AllTrails/Liz Koroskenyi
The path starts in Holliston near Blair Square and travels north and south. If you want to just explore the northern section, you’ll only have about 1.3 miles to cover. Otherwise, head south to encounter scenic Phipps Tunnel about a mile from the trailhead.

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This old tunnel was built to allow steam trains to travel beneath Highland Street. It has beautiful curved walls and is well-maintained. Along the southern stretch of the trail, you’ll find adjacent forests as well as bogs. You can visit Milford Pond on the right of the trail and Louisa Lake Park on the left.
AllTrails/Howie Hannigan
Most of the trail is paved with asphalt, packed cinder, or boards, making it easy for young kids or anyone who appreciates firmer ground.
AllTrails/Howie Hannigan
What are you waiting for? Lace up those hiking boots and explore!

Parking for the trail is located in Holliston at Blair Square off Front St. There’s also a municipal parking lot off Exchange Street Click here to find out more about accessing the trail from where you live.

You won’t regret trying out this gorgeous tunnel trail in Massachusetts. For more of the finest places to hike and explore in the state, check out these spots.

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