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Road cycling routes

Berkshire County

Cheshire Reservoir – Trail start loop from Pittsfield

Road cycling routes

Berkshire County

Cheshire Reservoir – Trail start loop from Pittsfield

Moderate

2.7

(28)

38

riders

Cheshire Reservoir – Trail start loop from Pittsfield

01:40

37.9km

360m

Road cycling

Moderate road ride. Good fitness required. Mostly well-paved surfaces and easy to ride. The starting point of the route is accessible with public transport.

Last updated: January 16, 2026

Waypoints

A

Start point

Train Station

1

8.64 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

2

22.2 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

3

22.4 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

4

30.9 km

Trail start

Highlight • Trail

Has bathroom and bike repair stand

Tip by

5

37.7 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

B

37.9 km

End point

Train Station

Way Types & Surfaces

Way Types

23.1 km

12.0 km

2.07 km

637 m

< 100 m

Surfaces

37.4 km

459 m

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Elevation

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

Highest point (390 m)

Lowest point (300 m)

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Weather

Powered by Foreca

Today

Thursday 12 November

7°C

1°C

98 %

Additional weather tips

It’s set to rain on your activity. Pack a waterproof jacket.

to get more detailed weather forecasts along your route

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