2.8
(20)
35
hikers
12:50
49.6km
290m
Hiking
The Upper Charles Trail offers a unique journey through Massachusetts' MetroWest suburbs, blending natural beauty with historical infrastructure. You'll traverse varied terrain, from paved sections in Milford to crushed stone and dirt paths in Holliston, passing by tranquil water bodies like Louisa Lake and through lush forests and bogs. Keep…
Last updated: June 9, 2026
Waypoints
Start point
Parking
Get Directions
8.16 km
Highlight • Cycleway
8.87 km
Highlight • Trail
Tip by
15.7 km
Highlight • Lake
Tip by
16.6 km
Highlight • Forest
Tip by
39.8 km
Wenakeening Woods
Nature Reserve
47.8 km
Sacred Heart of Jesus Parish
Place Of Worship
49.6 km
End point
Parking
Way Types & Surfaces
Way Types
38.4 km
6.76 km
4.33 km
< 100 m
Surfaces
23.8 km
15.0 km
6.86 km
1.92 km
1.76 km
246 m
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Elevation
Highest point (120 m)
Lowest point (50 m)
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Weather
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Today
Sunday 12 July
28°C
15°C
0 %
Additional weather tips
Max wind speed: 14.0 km/h
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This route was planned by komoot.
The trail connects several towns including Milford, Holliston, and Sherborn, offering various access points. While specific parking lots aren't detailed, you can often find parking near the historic depots or town centers that the trail passes through in these communities. Look for designated trail parking areas in Milford or Holliston.
Yes, this trail is widely considered easy and suitable for all fitness levels, including beginners and families. Its generally flat and well-maintained surfaces make it ideal for casual walks. Sections in Milford are paved, and much of the trail is crushed stone, making it accessible for strollers and various non-motorized uses.
The terrain varies along the route. Sections in Milford are primarily paved with asphalt. As you move into Holliston and towards Sherborn, the surface often transitions to well-maintained crushed stone or stone dust. While mostly flat due to its rail-trail nature, some segments in Milford can be hilly, and there are occasional unimproved dirt/mud sections, particularly in Holliston. Side paths can be more rugged.
The trail offers diverse New England scenery, including forests, bogs, and marshes. You'll pass by bodies of water like Louisa Lake, Milford Pond, and Wildcat Pond. Notable features include the eight-arch Bogastow Brook Viaduct and the historic Phipps Tunnel in Holliston. The trail also traverses conservation areas like the Dopping Brook Conservation Area and the Town Forest Recreation Area.
The trail's diverse habitats, including forests and wetlands, provide opportunities for wildlife viewing. You might spot rabbits, deer, various birds like blue herons and red-winged blackbirds, beavers, and muskrats in the adjacent natural areas.
Yes, the trail is generally dog-friendly. However, always ensure your dog is on a leash and that you clean up after them to maintain the trail's cleanliness for all users.
The trail is enjoyable year-round. Spring and fall offer pleasant temperatures and beautiful foliage. Summer is great for enjoying the lakes and ponds. In winter, it's suitable for cross-country skiing, though the trail is not cleared of snow and ice. Each season provides a unique perspective on the New England landscape.
No, there are no permits or entrance fees required to access the Upper Charles Trail. It is a public multi-use trail freely accessible to everyone.
Yes, the route also passes through sections of the East Coast Greenway (MA), the Milford Rail Trail Loop Segment, and the Bay Circuit Trail.
Beyond the main trail, there are opportunities to explore side paths that lead into extensive woodland networks. These include areas like Rocky Woods in Milford and Wenakeening Woods in Holliston, offering more natural and secluded hiking experiences for those seeking a bit more challenge.
Absolutely! The Upper Charles Trail is a multi-use path designed to accommodate various non-motorized activities. This includes jogging, cycling, and rollerblading on paved sections. In winter, it's also suitable for cross-country skiing, though it's important to note that snow and ice are not cleared.
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