Hiking the Cobbles via the Appalachian Trail – The Berkshires, Massachusetts

October 2024

Hiking the Cobbles via the Appalachian Trail – The Berkshires, Massachusetts

One of the best activities to add to your Berkshires itinerary is exploring the many hiking trails along western Massachusetts, some of which overlap with the famous Appalachian Trail. Completing these trails in the fall optimizes the opportunity to enjoy gorgeous fall foliage the New England area is known for.

And there really is no better trail than the Cobbles. The Cobbles consists of a moderate 1.8-mile out-and-back trail near Cheshire, Massachusetts. I do not recall where I originally stumbled upon this trail but I will say, information around it is very limited. Some resources indicated it was closed but reviews on AllTrails indicated it was very much still accessible. I got the impression this was more of a locals trail and not many tourists find their way to the Cobbles.

We followed the trailhead marker on Google Maps which took us through a residential neighborhood to find there was no parking access. Signs indicated that parking around here for the Cobbles was not viable and sent hikers about a mile in the opposite direction to the Ashuwillticook Rail Trail parking area and that did not seem right based on the reviews on AllTrails.

After looking back at the AllTrails reviews, some indicated there was a small parking lot off Notch Road so before we abandoned the Cobbles, we gave this a shot. And just a few minutes down the road we found the small parking lot and our plans of hiking the Cobbles were back. For your journey finding this parking lot, search for Chalet Wildlife Management Area Parking and you will have no issues securing parking. That being said, the parking lot is small but this trail seems so unknown that I do not think there will be any issues for your trip.

We were excited to find the parking lot but I have to say, we were hesitant as the trail looked pretty unmaintained. Maybe this was supposed to be closed like some references indicated but we decided to give it a try and could always turn back. The trail begins with a steady incline, but it is not too difficult. But then we came across a gate that also gave the impression we should not continue but a nearby sign indicated that there were no cars beyond the gate – I am not sure how it is even possible for a car to make it up here to begin with but we carefully walked around the gate and continued on.

After a few more minutes of climbing, we got our first indication that we were welcomed on this trail – a sign showing Notch Parking (the direction we came from) and the A.T. Northbound Trail (the direction we intended on going). With a relaxed feeling moving forward, we continued on the climb up the trail which we found to be an easy, steady incline.

After a short distance we reached another set of signs – to the right indicated the continuation of the Appalachian Trail and to the left was our destination, the Cobbles viewpoint. We followed the trail left and after a few steps, the trail sort of disappears and it is fair game to explore. We found the outlet to the rocks and the clearing emerged to the most spectacular viewpoint of the trip. The colors were simply stunning and you could see for miles up here. I could not believe for how short and easy this trail was, the view was just amazing.

We spent a bit of time exploring all the different viewpoints before heading back down the way we came, following the signs for Notch Road parking. It is easy to extend this trail and continue along the Appalachian Trail so if you are looking to spend more time here, that is definitely the way to do it. In total, we spent just over an hour to complete the entire Cobbles out and back. I was also amazed how few people we saw – the trail was virtually empty.

This trail is definitely a must when visiting the Berkshires. It is fairly easy to complete with some elevation gain and amazing sweeping views at the top. If you only have the opportunity for one hike during your trip, I would say the Cobbles is definitely the trail to choose for fall foliage viewing. I hope you enjoy this trail as much as we did!

Continue reading about our weekend in the Berkshires here!

Read all blog posts for the Berkshires here!

See our complete itinerary here!

Planning your trip? Check out the Perfect Fall Itinerary to the Berkshires here!