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Routes
Bike touring routes & trails
United States
Massachusetts
Worcester County

Upper Charles Trail Loop

Easy

4.6

(8429)

15,640

riders

Upper Charles Trail Loop

01:40

27.0km

130m

Cycling

Cycle the easy 16.8-mile Upper Charles Trail Loop, enjoying varied scenery, forests, and water views like Louisa Lake.

Last updated: February 26, 2026

Waypoints

A

Start point

Parking

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1

2.01 km

Town Forest Trails

Highlight • Trail

There is a great network of trails in this area, which connect with the adjacent parks, such as Adams Street Conservation Park.

The trails can be fairly technical, so wide …

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2

14.5 km

Upper Charles Trail

Highlight (Segment) • Trail

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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3

22.5 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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B

27.0 km

End point

Parking

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Way Types & Surfaces

Way Types

11.2 km

5.46 km

4.47 km

4.46 km

851 m

576 m

Surfaces

19.8 km

3.61 km

2.53 km

1.06 km

< 100 m

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Elevation

Elevation

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

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Weather

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Today

Wednesday 6 May

22°C

13°C

71 %

Additional weather tips

Max wind speed: 26.0 km/h

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This route was planned by komoot.

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Frequently Asked Questions

Where can I park to access the Upper Charles Trail Loop?

You can find convenient parking at Fino Field in Milford, which also offers restrooms. Other access points with parking may be available in the towns the trail passes through, such as Holliston.

Is the Upper Charles Trail Loop dog-friendly?

Yes, the Upper Charles Trail Loop is generally dog-friendly. Please ensure your dog is kept on a leash and that you clean up after them to maintain the trail for everyone.

What is the best time of year to cycle the Upper Charles Trail Loop?

The trail is enjoyable throughout the warmer months. Spring and fall offer pleasant temperatures and beautiful scenery, with autumn foliage being particularly striking. Summer is also great, but be prepared for potentially warmer weather.

Do I need any permits or pay entrance fees for this trail?

No, there are no permits or entrance fees required to access and enjoy the Upper Charles Trail Loop. It is freely accessible to the public.

What kind of terrain and surface can I expect on the trail?

The trail offers a varied experience. While it largely follows a former railroad bed, providing a relatively level grade, the surface changes. Expect mostly paved asphalt sections, especially in Milford. Unpaved portions, particularly in Holliston, consist of packed dirt, cinder, or crushed stone. Some segments might be rougher, with ballast, dirt, or mud, especially after rain. Bikes with wider tires or hybrids are recommended for comfort.

How difficult is the Upper Charles Trail Loop for cyclists?

The Upper Charles Trail Loop is generally considered an easy route for touring cyclists, suitable for a wide range of fitness levels. While the overall elevation gain is modest (around 127 meters over 27 km), some unpaved or wet sections might present a slight challenge. It's a great option for beginners and casual riders.

What are the notable features and sights along the Upper Charles Trail Loop?

The trail offers diverse scenery and points of interest. You'll pass through forests and bogs, with opportunities for wildlife viewing. Along the Milford section, you'll skirt Milford Pond, Louisa Lake, and Wildcat Pond. In Holliston, look for the historical Phipps Tunnel and the beautiful Bogastow Brook Viaduct with its eight arches. You'll also encounter sections of the Town Forest Trails and the main Upper Charles Trail.

Is the Upper Charles Trail Loop suitable for families with children?

Yes, many parts of the Upper Charles Trail Loop are well-suited for families with children, especially the paved sections. The generally gentle grade and varied scenery make it an enjoyable outing. Just be mindful of the unpaved sections, which might be a bit rougher for very young riders or those on road bikes.

Does the Upper Charles Trail Loop connect with other trails?

Yes, the route primarily follows the Upper Charles Trail for a significant portion. It also includes sections of the Milford Byway and the Holliston Highway, among other smaller local paths.

Are there amenities like restrooms or places to eat along the route?

Restrooms are available at Fino Field in Milford, a common access point. As the trail passes through several towns, you'll find opportunities for cafes, pubs, and other amenities nearby, especially in the town centers that the trail skirts.

What should I bring for a cycling trip on this trail?

For a comfortable ride, bring plenty of water, especially on warmer days, as water sources might not be consistently available directly on the trail. A helmet, basic bike repair kit, and appropriate clothing for the weather are also recommended. If you plan to tackle the unpaved sections, consider a bike with wider tires for better stability and comfort.

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