July 19, 2011

Berkshire Cycling: Windsor Loop 1

26 Miles                Paved and dirt roads

Start: Rt. 9, Windsor
Towns: Windsor, Peru, Hinsdale                     

This is an absolutely wonderful ride. Though the photos are only of flat stretches, the rural roads wind up, down and around these rolling hillsides, with very little traffic. It was hilly enough and a good length for the three of us to ride. I often ride solo and so particularly enjoyed the chance to ride with friends.

We started near Route 9 in Windsor, and headed east to East Windsor Road. Turn south and follow it to Pierce Road. After turning right onto Pierce, the road quickly went into Peru and became East Windsor Road. The roads around here do that, changing names when they change towns. There are three Middlefield Roads that I know of, all unconnected, that travel to Middlefield from its neighboring towns.

At the fork in the road we continued to the left onto North Road, which ends at Rt. 143, at the top of the Peru hill. Peru is in fact named after the eponymous country, because it is so high. In the winter is is also so cold. Continue straight across Rt. 143, onto South Road, and follow it to Middlefield Road/Skyline Trail. Turn right and head downhill into Hinsdale. At Creamery Road turn right to its dead-end on Rt. 143. On 143 head back east for a very short ways, then left onto New Windsor Road, left onto Stone House Rd., which turns into Frank Schnopps Road. Right onto Windsor Road, which becomes Main Dalton Road and follow it back to Route 9. Right to the general store.

Take a map! There is no road list here because it is all in the text above. This is a very fun respite from the crowds of central and southern Berkshire County, and even more, from their cars. Also, take whatever water or snacks you might want, as there are no stores on the route. 

Berkshire Rides List 


  1. Hi!
    Such fun to find you've ridden a loop I know. I grew up in Dalton and still have family in the Berkshires.
    I bring my bike with me when I drive up from VA so I can get some hill work in!

    1. Hi! Thanks for taking the time to comment.

      I grew up in VA and sometimes take my bike when I visit my sister!


Please leave a comment, it's great to hear from you and makes the site more fun and informative for other readers!