A Hidden Hike in the Beautiful Berkshire Mountains

Remember how one secret to a happy relationship is to take exciting weekend trips? Let’s add to that: Make your relationships even more thrilling by including hilarious and brilliant family members in your travel plans! Ensure that all parties involved enjoy hiking and making dramatic poses in pictures. And eat a lot.

So it was that my husband Colin and I drove three hours on an October Friday evening from Boston to the tranquil Berkshire Mountains to meet with my beloved cousins, Andrew and Eric. (You may know Eric because you’re one of the thousands of people who read about his cutting-edge pineapple technology.)

It turns out that Eric and Andrew are trip-planning geniuses. To prep, Andrew scoured TripAdvisor to find the top-rated hotel in the area: a gem in Cheshire called Harbour House. (Note: This is not a sponsored post. The delightful B&B owner, Eva, had no idea of my world fame when she housed me and fed us fluffy pumpkin-chocolate-chip muffins.)

When Colin and I arrived late on Friday night, we learned that Andrew had already schemed with Eva about where to hike the next morning: “Cheshire Cobbles!” my cuz declared. I immediately pictured Cheshire Cats tap dancing around cobblestones and wee elven cobblers hammering away with little shoe-tools.

Eva showed us the way to the “Cobbles” in her car. It was just a few minutes’ drive from the downy bed where we’d slept that night, and the sunny dining room in which we’d stuffed ourselves silly at the ten-part breakfast alongside travelers from Germany and Austria. As you can tell from the photo below, I was awkwardly wearing only long underwear during this hike. I’m not really sure why except that it was cosy.

Through the crunchy leaves and streaming gold sun, we hiked! Luckily, Colin is like a forest wolf and can track the “Blazes” (what the cool kids call, “Colored thingies that tell you which way to walk when you’re in the middle of nowhere”), so we stayed un-lost. When we emerged at the top of the hill (“Cobble?”) what a vista we saw! Do you enjoy our poses?

Tromping back down the hill, exhilarated, we talked about our school year so far (Eric and Colin are teachers, too), climbed boulders, and took silly and also luscious photos. How lucky we felt that Eva had steered us towards the hidden hike of Cheshire Cobbles! Just like that crazy Cheshire Cat, you can’t help but grin wide when walking in a place like this.

Are you liking our Western Massachusetts escapade so far? Well, stay tuned, because Part Two (replete with an epic bike path, gorging ourselves at a farm stand, and a world-famous museum) is coming next! Until then, I look forward to your comments. What hidden tourist gems have you found thanks to the kind suggestion of a local? Have you also spent time around the Berkshires, MA? Do you, too, enjoy dramatic photo poses? Comment away!