Cheshire Reservoir – Ashuwillticook Rail Trail Head loop from Pittsfield

Cheshire Reservoir – Ashuwillticook Rail Trail Head loop from Pittsfield

Moderate

2.7

(24)

riders

Cheshire Reservoir – Ashuwillticook Rail Trail Head loop from Pittsfield

03:46

85.6km

680m

Road cycling

Moderate road ride. Good fitness required. Some segments of this route may be unpaved and difficult to ride. The starting point of the route is accessible with public transport.

Last updated: November 26, 2025

Tips

Temporary access restrictions

Includes segments with temporary access restrictions.

After 44.2 km for 244 m

Customers only

Waypoints

Start point

Train Station

Get Directions

11.6 km

Berkshire Pond

Lake

13.6 km

U.S. Bicycle Route 7 — Cheshire Reservoir section

Highlight (Segment) • Cycleway

The U.S. Bicycle Route 7 (USBR 7) is a super good, north-south bike trail that follows the Western New England Greenway through Connecticut, Massachusetts, and Vermont. This section in Massachusetts …

Tip by

15.8 km

Cheshire Reservoir

Highlight • Lake

Cheshire Reservoir captivates riders with its tranquil beauty. The scenic reservoir, nestled in the Berkshires, offers stunning views along the route. Cyclists can enjoy a peaceful ride surrounded by nature, …

Tip by

28.8 km

Trail end

Highlight • Trail

End of trail at a T intersection

Tip by

29.7 km

Ashuwillticook Rail Trail Head

Highlight • Cycleway

Here's the Trail Head of the Ashuwillticook Rail Trail. The trail is perfectly smooth and easy to use for families.

Tip by

47.8 km

The Clark Art Institute

Highlight • Monument

Super great art museum with a lot of French impressionists like Auguste Renoir and Claude Monet. There are also many sculptures by Auguste Rodin.

Translated by Google •

Tip by

52.2 km

Green River Wildlife Management Area

Nature Reserve

54.9 km

Green River Wildlife Management Area

Highlight • Natural

Close to the confluence of the Ohio and Green rivers, this area features gently rolling green hills, contributing to its picturesque scenery. Committed to supporting fish, wildlife, and habitat conservation, it plays a role in maintaining the area's natural beauty.

Tip by

80.8 km

Onota Lake

Highlight • Lake

A stunning view awaits as you pedal over Onota Lake on the Dan Casey Memorial Drive. It's owned by the City of Pittsfield, so it's open to the public for swimming and water sports.

Tip by

85.5 km

Joseph Scelsi Intermodal Transportation Center

Highlight • Rest Area

The Joseph Scelsi ITC exemplifies the journey of many train stations across the US. From grand historical structures to modern intermodal centers, they reflect the evolution of transportation needs and …

Tip by