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Cheshire Reservoir – Ashuwillticook Rail Trail Head loop from Buckland

Cheshire Reservoir – Ashuwillticook Rail Trail Head loop from Buckland

Hard

2.5

(24)

riders

Cheshire Reservoir – Ashuwillticook Rail Trail Head loop from Buckland

07:13

139km

2,420m

Road cycling

Hard road ride. Very 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: December 18, 2025

Tips

The surface along some of this route may not be suitable

Some segments of your route comprise a surface that may not be suitable for your chosen sport.

After 38.3 km for 278 m

After 39.2 km for 236 m

After 39.7 km for 278 m

Waypoints

Start point

Bus stop

Get Directions

4.48 km

Bissell Bridge

Highlight • Bridge

Historic covered bridges such as this one are traditional in the area, and it is great to see them maintained. The Bissel Covered Bridge was built in 1881. By the …

Tip by

21.1 km

Hoosac Tunnel East Portal

Highlight • Monument

The Hoosac Tunnel is a working 4.75-mile (7.64 km) active freight railroad tunnel in western Massachusetts. The East Portal of the tunnel can be found in the town of Florida. …

Tip by

39.3 km

Natural Bridge State Park Waterfalls

Highlight • Waterfall

Probably more impressive to ride/drive up through McCauley Road. You can also access it from Natural Bridge or Hudson Brook Lane Road on foot or on a bike (which is …

Tip by

57.4 km

Mount Greylock

Highlight • Summit

Mount Greylock is the tallest peak in Massachussets. On a clear day, you can see up to 90 miles in the distance.

At the peak, there is a visitor center, restrooms and a scenic viewing area.

Tip by

58.8 km

Rockwell Road

Highlight (Segment) • Cycleway

78.8 km

Berkshire Pond

Lake

82.6 km

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

96.1 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

99.6 km

Viewpoint

117 km

Plainfield Pond

Highlight • Lake

Plainfield Pond in Massachusetts offers a calm retreat for visitors and cyclists. Surrounded by wooded landscapes, the pond provides a peaceful setting for a bike ride break. The scenery includes …

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139 km

End point

Bus stop

Way Types & Surfaces

Way Types

81.4 km

21.1 km

19.4 km

16.5 km

352 m

< 100 m

Surfaces

129 km

8.34 km

575 m

322 m

158 m

Elevation

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

Weather

Today

Wednesday 27 May

27°C

14°C

17 %

Additional weather tips

Max wind speed: 19.0 km/h

to get more detailed weather forecasts along your route

Our route recommendations are based on thousands of hikes, rides, and runs completed by other people on komoot.

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Cheshire Reservoir – Ashuwillticook Rail Trail Head loop from Buckland

Bissell Bridge

Hoosac Tunnel East Portal

Natural Bridge State Park Waterfalls

Mount Greylock

Rockwell Road