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Routes
Hiking trails & Routes
United States
Massachusetts
Middlesex County

Upper Charles Trail

Hard

2.8

(20)

35

hikers

Upper Charles Trail

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

A

Start point

Parking

Get Directions

1

8.16 km

Milford Rail Trail Loop Segment

Highlight • Cycleway

2

8.87 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.

Tip by

3

15.7 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 …

Tip by

4

16.6 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 …

Tip by

39.8 km

Wenakeening Woods

Nature Reserve

47.8 km

Sacred Heart of Jesus Parish

Place Of Worship

B

49.6 km

End point

Parking

Loading

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

Elevation

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

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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Frequently Asked Questions

Where can I park to access the Upper Charles Trail?

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.

Is the Upper Charles Trail suitable for beginners or families?

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.

What is the terrain like on the trail?

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.

What can I see along the route?

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.

What wildlife might I encounter?

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.

Is the Upper Charles Trail dog-friendly?

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.

What is the best time of year to visit?

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.

Are there any permits or entrance fees required?

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.

Does the trail intersect other well-known paths?

Yes, the route also passes through sections of the East Coast Greenway (MA), the Milford Rail Trail Loop Segment, and the Bay Circuit Trail.

Are there any side trails or more rugged options available?

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.

Can I use the trail for activities other than hiking?

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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