Chesterfield Gorge Trail: TDG Trail Report 8/24/25

Just a quick entry on this fun little “hike” we did on a beautiful Sunday at Chesterfield Gorge in the remote “Hill Towns” of the Berkshire plateau. I used the quotes because it is more like a walk. It follows an old dirt road along the very picturesque Westfield River. On this Sunday folks were hanging on the side of the river, sunbathing, picnicking and such. Incredible scene!

The rocky gorge part is pretty dramatic is right near the trailhead/parking lot. There are some big cliffs on either side, and you can walk right along the edge for a bit (before you start walking on the dirt road). And it goes on for like 8 miles. We only walked a bit on it, but you could go for hours…

The ride through the roads of the Hill Towns are part of the fun. Such a nice day for blasting music and riding with the windows down. Classic summer in the Berkshires!

I might not guide this one, but for people looking for a nice easy beautiful walk in an incredible natural setting this is a great option. Enjoy!

Until next time…

-TDG

Oh and a fun tip—stop at the Old Creamery Co-Op on the side of the road in little Cummington, MA. Great ice cream and other goods.