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Upper Charles Trail – Upper Charles Trail loop from Medway

Upper Charles Trail – Upper Charles Trail loop from Medway

Moderate

3.1

(22)

riders

Upper Charles Trail – Upper Charles Trail loop from Medway

01:48

38.8km

210m

Road cycling

Moderate road ride. Great for any fitness level. Some segments of this route may be unpaved and difficult to ride. The starting point of the route is accessible with public transport.

Last updated: May 13, 2026

Tips

The surface along some of this route may not be suitable

Some segments of your route comprise a surface that may not be suitable for your chosen sport.

After 7.19 km for 5.47 km

After 12.7 km for 503 m

Waypoints

Start point

Bus stop

Get Directions

8.29 km

Upper Charles Rail Trail

Highlight (Segment) • Structure

The Upper Charles Rail Trail is a 13.5-mile rail trail that consists of a packed dirt and cinder path the entire time. This section of the trail passes through the …

Tip by

10.9 km

Former railroad track the Upper Charles Trail is currently over 13 miles long. It eventually plans to connect the communities of Milford, Ashland, Sherborne, Holliston, Framingham and Hopkinton. It will …

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17.5 km

Upper Charles Trail

Highlight (Segment) • Trail

The Upper Charles Trail is a work in progress trail build. It will one day total 24 miles, linking the communities of Milford, Ashland, Sherborn, Holliston, Framingham, and Hopkinton. Simply …

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19.0 km

Louisa Lake

Highlight • Lake

There is a bit of everything here at Louisa Lake. It is very scenic area and along with nearby Milford Pond, it provides a great venue for a variety of …

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22.9 km

Upper Charles Trail

Highlight • Trail

The Upper Charles Trail in Massachusetts offers cyclists a scenic route through historic mill towns, verdant woodlands, and along the Charles River. This multi-use trail spans diverse landscapes, showcasing the region's industrial heritage.

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25.8 km

Town Forest Recreation Area

Highlight • Forest

Town Forest is a forested recreation area in the quaint town of Milford. It should not be mixed up with its nearby namesake Town Forest Nature Reserve. Town Forest recreation …

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38.8 km

End point

Bus stop

Way Types & Surfaces

Way Types

18.2 km

8.43 km

6.11 km

4.89 km

1.16 km

< 100 m

Surfaces

32.7 km

4.87 km

784 m

271 m

158 m

Elevation

Nothing selected – click and drag below to see the stats for a specific part of the route.

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Our route recommendations are based on thousands of hikes, rides, and runs completed by other people on komoot.

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Upper Charles Trail – Upper Charles Trail loop from Medway

Upper Charles Rail Trail

Upper Charles Trail

Upper Charles Trail

Louisa Lake

Upper Charles Trail

Town Forest Recreation Area

Nearby routes

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