You don’t need much to sell Cheshire Cobble hike: it’s a slam-dunk short hike with an incredible payoff. It’s a quick 45 minutes (give or take) moderate climb up to one of the best overlooks in the whole Berkshire region. Oh, and it’s a segment of the Appalachian Trail. Wow, here’s a little invigorating walk where you get some forest bathing time, just a tad bit of uphill hiking exercise, you get to hike the world-famous “AT”, and, finally, a stunning vista.

Starting in the little Berkshire hamlet of Cheshire, we join the Appalachian Trail as it crosses the Ashuwillticook Rail Trail (great 15-mile paved trail). From there, after walking through a neighborhood for about ten minutes, we enter the forest and gain around 700 feet over 1.25 miles—just a moderate ascent as we get higher. Nothing steep, just a few big rocks to walk around under the “cobble”—the crumbling of the granite overhang above that serves as our viewing platform. We can go a bit further south to the top of the cobble and another view if we are feeling up to it. About 1.5 hours for the whole out-and-back hike.