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.

Read about one of my Cheshire Cobble hikes on TDG Blog.

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.