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Routes
Road cycling routes
United States
Massachusetts
Middlesex County

Upper Charles Trail

Easy

3.5

(9)

50

riders

Upper Charles Trail

00:40

15.5km

90m

Road cycling

Embark on an easy road cycling journey along the Upper Charles Trail, a 9.6 miles (15.5 km) route that promises a pleasant 40-minute ride. You'll experience a gentle elevation gain of 293 feet (89 metres) as you pedal through varied New England landscapes. The trail offers scenic views, following parts of the Charles River and passing by natural features like Louisa Lake. Keep an eye out for local wildlife as you cycle through woodlands and marshes. It's a straightforward and enjoyable experience, perfect for a relaxed outing on your racebike.

Before you set out, know that the Upper Charles Trail is generally well-maintained, though you might encounter some unimproved sections. This route is designed for easy access, making it simple to start your ride. You'll find plenty of benches and pullouts along the way, offering convenient spots to pause and rest. When you are passing other trail users, remember to use audible signals and always yield to pedestrians to ensure a smooth experience for everyone.

This trail stands out for its blend of natural beauty and historical significance. As you cycle, you'll pass by impressive historic sites, including the notable eight-arch stone bridge located in Holliston. The route provides a unique opportunity to connect with the region's past while enjoying the present-day tranquility of the Charles River area. It's a great option if you're looking for a ride that combines gentle exercise with interesting sights.

Last updated: April 23, 2026

Waypoints

A

Start point

Parking

Get Directions

1

8.05 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 another brilliant rails to trails project that to date (2018) has more than 13 miles of the trail completed. The surface is mainly asphalt and crushed stone so it is best done on a gravel bike.

Tip by

2

9.48 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 recreational activities, especially bicycling. Nearby is the Upper Charles Trail, a super good cycling trail.

Tip by

3

10.4 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 area is situated near to the two cemeteries of North Purchase Street Cemetery and Pine Grove Cemetery. You can hike and run here but as far as cycling is concerned you can cycle through it on the Upper Charles Trail.

Tip by

B

15.5 km

End point

Parking

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Way Types & Surfaces

Way Types

6.09 km

4.70 km

4.68 km

Surfaces

12.0 km

3.47 km

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Elevation

Elevation

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Friday 22 May

18°C

7°C

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Frequently Asked Questions

Where can I park to access the Upper Charles Trail?

While specific parking areas are not detailed, the trail connects the towns of Milford, Holliston, and Sherborn. You can typically find parking near trailheads or public access points within these towns. For example, the Milford section is easily accessible.

Is the Upper Charles Trail dog-friendly?

Yes, the Upper Charles Trail is a multi-use pathway, and dogs are generally welcome. Please ensure your dog is on a leash and that you clean up after them to maintain the trail for all users.

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

The trail offers a pleasant experience throughout the warmer months. Spring and fall provide comfortable temperatures and beautiful New England scenery, especially with changing foliage. Summer is also suitable, but be prepared for potentially warmer weather.

Do I need a permit or pay an entrance fee to use the Upper Charles Trail?

No, there are no permits or entrance fees required to access and use the Upper Charles Trail. It is a public multi-use path.

What is the surface like on the Upper Charles Trail, and is it suitable for road bikes?

The trail surface varies significantly. The Milford section is primarily asphalt and generally flat. As you enter Holliston, it transitions to crushed stone, packed dirt, and fine gravel. While road bikes with 25mm tires can navigate some crushed stone sections, certain parts in Holliston can be rougher, with ballast and areas that might require off-road tires or front shocks for comfort and safety. Some short on-road segments are also marked as bike routes.

What natural features and historic sites can I see along the trail?

The trail offers a bucolic journey through New England nature. You'll pass by natural features like Louisa Lake and Milford Pond, woodlands, and marshes, with opportunities to spot wildlife such as deer, blue herons, and beavers. Historic sites include the foundation ruins of granite cutting sheds in Milford, the impressive eight-arch stone bridge, and the historic Phipps Tunnel in Holliston.

Are there sections of the Upper Charles Trail suitable for family cycling?

Yes, the paved and generally flat sections in Milford are ideal for young children and casual family rides. However, be aware that the surface changes to crushed stone and rougher terrain in Holliston, which might be more challenging for very young riders or those on road bikes.

Does the Upper Charles Trail connect with other trails?

Yes, the route primarily follows the Upper Charles Trail itself. It also briefly intersects with sections of the East Coast Greenway (MA) and various smaller local paths like the Orange Trail - College Rock Park and College Rock Run.

What makes the Upper Charles Trail a unique cycling experience?

The trail stands out for its diverse experience, blending paved and unpaved sections, natural scenery, and historical points of interest. It features notable structures like the eight-arch stone bridge and the historic Phipps Tunnel. As a multi-use rail trail, it connects several towns, offering a valuable and scenic route through Massachusetts' MetroWest suburbs.

Are there places to eat or drink near the Upper Charles Trail?

The trail connects Milford, Holliston, and Sherborn. You can find various cafes, restaurants, and pubs in these towns, particularly in the more developed areas of Milford and Holliston, which are easily accessible from the trail.

What should I bring for a ride on the Upper Charles Trail?

Given the varied terrain, it's advisable to bring a bike suitable for mixed surfaces, especially if you plan to cover the entire length. Water, snacks, sun protection, and a basic repair kit are always recommended. If cycling in Holliston, consider tires wider than 25mm for better comfort on crushed stone and packed dirt sections.

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