Berkshire Cycling: Washington Skyline Loop 1

31 miles                 Paved  roads

Start: Rt. 8, Washington

Towns: Washington, Becket, Chester, Middlefield, Hinsdale

Skyline Trail in Middlefield

This proved to be the most enjoyable cycling so far this year, mostly riding on Skyline Trail in Chester, Middlefield, Hinsdale. The ride took me across Wade Inn Road, which could be fun, if only the road surface were repaired. It is a mess and my travel was cautious. 

Abandoned mill in Chester

I rode to Skyline Trail via Chester, a town on Route 20 that I don’t often get to. It boasts a fine, small, summer theater company, The Chester Theatre Company, where we’ve seen a handful of excellent one-act plays. 


Chester is at quite a lower altitude than Washington, located on both Rt. 20 and the Westfield River, with the major east-west rail line running through it. You can tell how much lower the town is by the width of the river here; they don’t come this wide at home. It was settled in the 1750s, the railroad arrived in the 1840s, and for a time it had a busy granite industry. The town must have known more prosperous days, with this old, abandoned-looking mill building probably part of them. 

Westfield River in Chester

My ride turned quickly back north, climbing up Reservoir/Middlefield Road to Skyline Trail, a challenging climb.

Historic center of Middlefield

Once up to Middlefield, I turned left onto Skyline Trail, which goes through the village of Middlefield. This road rolls along the top of the ridge and is a lot of fun. You can see the ridge in Washington from the town of Middlefield. And the two towns are similar, both have historic, white-painted wooden town halls that are now closed. Both town halls are now in the old grammar schools, brick buildings that look to date from the 1970s and are now closed. Both modern town halls are good places to stop and fill a water bottle, as neither town has any stores.

Skyline Trail continues to Rt. 8 in Hinsdale, where I turned left to return to Washington.

Roads; Rt 8 South/ Wade Inn east/ Rt. 20 east/ Middle field Rd. (Reservoir Rd.) north/ Skyline Trail / Route 8 south. Click here for this route on Map My Ride, with cue sheet, map and climbing details.



Berkshire Rides List