Upper Charles Trail Loop
Upper Charles Trail Loop
4.6
(8429)
15,640
riders
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
Start point
Parking
Get Directions
2.01 km
Highlight • Trail
Tip by
14.5 km
Highlight (Segment) • Trail
Tip by
22.5 km
Highlight • Lake
Tip by
27.0 km
End point
Parking
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
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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.
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.
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.
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.
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.
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.
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.
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.
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.
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.
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.
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.