Routes

Planner

Features

Updates

App

Login or Signup

Get the App

Login or Signup

Routes
Hiking trails & Routes
United States
Massachusetts
Middlesex County

Upper Charles Rail Trail

Moderate

4.9

(1279)

7,288

hikers

Upper Charles Rail Trail

03:35

14.0km

70m

Hiking

Hike the Upper Charles Rail Trail, a moderate 8.7-mile route featuring diverse scenery, wildlife, and historical landmarks.

Last updated: February 26, 2026

Waypoints

A

Start point

Get Directions

6.99 km

Wenakeening Woods

Nature Reserve

B

14.0 km

End point

Parking

Loading

Way Types & Surfaces

Way Types

13.5 km

285 m

< 100 m

< 100 m

< 100 m

Surfaces

9.26 km

3.63 km

367 m

355 m

230 m

136 m

Sign up to see more specific route details

Sign up for free

Elevation

Elevation

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

Sign up to see more specific route details

Sign up for free

Weather

Powered by Foreca

Today

Wednesday 8 July

26°C

15°C

0 %

Additional weather tips

Max wind speed: 12.0 km/h

to get more detailed weather forecasts along your route

Comments

guide_signup

Want to know more?

Sign up for a free komoot account to join the conversation.

Sign up for free

This route was planned by komoot.

Save

Edit route

Download GPX

Move start point

Print

Share

Embed on a website

Report an Issue

Report restricted access

Frequently Asked Questions

Where are the main access points and parking for the trail?

The Upper Charles Rail Trail offers ample parking at various points along its length, as it connects several towns. Specific trailheads and parking areas can be found in towns like Milford and Holliston, providing convenient access to different sections of the path.

Is the trail suitable for beginners or families?

Yes, the trail is considered easy and is highly suitable for beginners and families. It has an 'Easy' physical rating and a 'Green' climb difficulty, making it accessible for a wide range of users, including those with strollers or wheelchairs on its main paved sections.

What is the terrain and surface like on the trail?

The terrain is generally flat, typical of a rail trail, with minimal elevation changes. The surface varies; the Milford portion is largely paved with asphalt, while the Holliston section consists mainly of packed dirt, fine gravel, or stone dust. Some side trails offer a more rugged, singletrack experience.

What kind of scenery and wildlife can I expect to see?

The trail meanders through diverse scenery, including woodlands, marshes, and often parallels the Charles River. You can expect to see various wildlife such as rabbits, deer, birds, snakes, toads, geese, blue herons, beavers, and muskrats. It also passes picturesque bodies of water like Milford Pond, Louisa Lake, and Wildcat Pond.

What notable features or historical landmarks are along the route?

The trail, converted from an abandoned railroad bed, features several historical landmarks. These include the distinctive Phipps Tunnel, known for its curved walls, and the impressive Bogastow Brook Viaduct, a stone bridge with eight arches. A side path also leads to the Fatima Shrine for a cultural detour.

When is the best time of year to hike the trail?

The trail offers beauty year-round. Autumn provides 'perfect autumn colors,' while winter can offer quiet, snowy landscapes suitable for snowshoeing. Spring and summer are also excellent for enjoying the diverse scenery and wildlife. The best time depends on your preferred outdoor activity and aesthetic.

Is the Upper Charles Rail Trail dog-friendly?

While the trail is a multi-use path, specific dog rules can vary by town section. Generally, dogs are welcome but should be kept on a leash and owners are expected to clean up after their pets. Always check local signage for any specific regulations.

Are there any permits or fees required to use the trail?

No, there are no permits or entrance fees required to access or use the Upper Charles Rail Trail. It is a publicly accessible multi-use path maintained by local communities.

Does the trail connect with other paths?

Yes, the route also passes through sections of the Upper Charles Trail, the East Coast Greenway (MA), and the Bay Circuit Trail, making it part of a larger network of paths for extended adventures.

Are there any sections of the trail that offer a more rugged experience?

While the main trail is generally easy, numerous side trails branch off into areas like Rocky Woods in Milford and Wenakeening Woods in Holliston. These side paths can be singletrack and offer a more rugged experience for those seeking a greater challenge.

Is the trail a loop or an out-and-back route?

The Upper Charles Rail Trail is primarily an out-and-back route, spanning approximately 13.4 miles in its current form. However, its connection to other trails and its linear nature allow users to customize their distance and turn around at any point.

Nearby routes

Easy

4.5

164

Fresh Pond Reservation Loop Trail

01:23h

5.44km

20m

Explore
RoutesRoute plannerFeaturesHikesMTB TrailsRoad cycling routesBikepackingSitemap
Download the app
Follow Us on Socials

© komoot GmbH

Privacy Policy