Roaming About

A Life Less Ordinary

Walking and Seeing the Real Berkshires in Connecticut

The Berkshire Mountains in Connecticut

The Berkshire Mountains in Connecticut

Mark and I had been living in the “foothills of the Berkshires” for almost two months, barely noticing those geography defining Berkshire Mountains. Sure, each time we drive from our house sit to the town of Kent to run errands, our ears pop and we don’t need any fuel to reach the bottom of the road, but the cold weather, sometimes gray, sometimes snowy had not allowed us to walk up to any viewpoints during our weekend outings with the dogs. When the sun set, I could often spot what I thought to be a purple hued hill top in the distance, through the barren trees around the house. I wanted to stand on top of one of those hills…

Sunset in our yard - somewhere with a top of the hill on the horizon

Sunset in our yard – somewhere on the horizon is the top of a hill

That was anticipated last weekend, when Mark and I decided to hike Macedonia Brook State Park in earnest. Previously, we had strolled along one of the old logging roads there, but this time, we set out on the white trail, easily reachable from one of the parking areas. Based on a map we “memorized” at home, we parked in the third lot counting from the southern entrance and immediately started on the easy stretch towards the old road. We kept the dogs on leash through the forest here, since it was quite busy on this sunny Saturday. Another .2 mile stroll on the orange/white road brought us to the start of Cobble Mountain Trail. The tough part would soon begin.

We followed the white markers, painted on trees, and started the climb zigzagging up the mountain. The dogs charged ahead, showing us the way, while we had our hands free to help with the ascend. The path was quite slippery, but rock ledges and tree roots helped out when necessary. After an hour or so, we reached a split. The blue trail kept going up over a rocky face, the white one led back down the mountain. The four of us joined the blue trail to reach a windy viewpoint from where we had a good look over the Berkshires. It had certainly be worth the climb.

Based on the map, we were supposed to follow the ridge line for a bit (blue trail) to another viewpoint, before reaching the green trail back to the old road (orange trail), so we could make a loop back to the car. Since we couldn’t quite figure out the exact direction of the blue trail on top of Cobble Mountain, and we had noticed that the white trail went down a different way, we descended, following new white markers on trees and rocks. All the while, we were confused about this white route, which appeared to be a loop as well. What went wrong? Which part was not on the map? Little Mickey was a good sport again, jumping down massive rocks, ears flapping in the pleasant mountain air and Henry was happy as a deer in the woods. It was a slippery track, with moss and a thick carpet of leaves covering up the rocks and the steep slope. We were glad to have come up the other way.

Towards the end/the beginning of the white trail, our little mystery was solved. Unbeknownst to us, we had veered off the main trail, and stepped over some tree trunks on the ground, presumably put in place to block that section of the trail. I guess the dogs knew about this alternative way up the mountain. 🙂 The white markers had still been in place, so we didn’t know any better. We assume we followed an old hiking trail to the top and took the “right” one back down. It made for a more interesting and diverse walk this way – I love circular trials better than going the same way in and out. Next, we want to hike the full length of the blue trail, encompassing all of Macedonia Brook State Park. We might have to wait until spring for that, though, or at least until all our tired muscles, feet and paws are rested.

(This post is submitted to Jo’s Monday Walk)


  1. Hooray! You made it! 🙂 Nobody has ever taken me to the Berkshires before so thank you very much. Welcome to my walks. 🙂

  2. Looks like a great walk!

    On another note, not sure if you know about the Make Like an Ape Man blog – They split their time between their boat, their Westfalia van and house/pet sitting. Thought you might be interested in checking them out from the house/pet sitting angle.

    • Ellen, thanks for the link! Looks like we have a lot in common with Greg and Duwan: cruising by boat, traveling by camper (in our past and future) and house sitting! You are a great match maker. 🙂

  3. I am delighted to see that you have joined Jo’s walks! And what a fabulous entry. I miss New England!!!

    • Yes, Lisa. I finally made it a priority to join Jo on her walks and maybe I can even make this a weekly event… Just like some other themes here and there. Looks like I might get even busier… When are you going on your next walk? Looking forward to reading about your city adventures!!!

      • You are in the perfect location for it!

        I am hopeful that we can head to the Blue Mountains sometime in March. If we do, there will definitely be a ‘Jo’s Monday Walk’ in that trip. Fingers crossed.

  4. Ah, now I see where the connection was made! I recognise liking this post via Jo’s Monday Walks. We stayed a couple of nights in the Berkshires on my very first visit to the US which caught my interest.

    • The Berkshires are pretty nice for hiking. Our next house sit is also located in these mountains, but in MA instead of CT, so more walks to follow in the future! 🙂

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