Hiking Bear Mountain / Weekend in the Berkshires
Hiking Bear Mountain, Connecticut | Weekend in Great Barrington, MA | May 2025
After a peaceful night on Mount Washington – Massachusetts, not New Hampshire – we had a slow morning. The rain had let up enough to let me walk Charlotte around while Jess took care of the morning chores. We could definitely tell it was Memorial Day weekend though. It was barely 8 and there were already hikers showing up for short backpacking trips through the area.
We had the morning to kill before my brother would be ready for us to show up. So I figured we could go down to the CT-MA state line and I could hike Connecticut’s not-quite-the-highest mountain. And that way we could also claim another state for the annual count.
We have already been to Connecticut’s highest point in 2017, but it is on the slope of a mountain, the summit of which is in Massachusetts and overall an underwhelming objective. But back when we were still figuring out hiking and peak-bagging, I found some misinformation that claimed that Bear Mountain was the highest point in CT: letterbox clues, hiking guides, etc. And in all of these resource’s defense, there is a sizeable placard on the summit claiming it to be ‘the highest ground’ in CT – a fact that was not disproven until 1940.
So, for the sake of hiking something new, we parked near the State Line (which was already crowded), and I followed a network of trails until I caught up with the Appalachian Trail heading North. I lucked out in that the cloud layer was just above the peak, so when I reached the summit I actually had decent views of the surrounding mountains and valleys! I chatted with some of the hikers as they came and went, and then attempted several letterboxes. But try as I might, I came up with nothing. And to add insult to injury, it started to rain…hard. I decided it was time to go, but decided to keep heading North along the AT back into Mass before following an access trail back to Jess and Charlie.
By the time I had made it back, the rain had let up, so I joked that, technically, I had been to Connecticut for the year and Jess hadn’t, so we all walked the 100 yds down the road until we reached the road gate that presumably marks the state line.
Satisfied and having been told by my brother that he should be home soon, we turned back North and drove to his place where he graciously allowed us to park in his yard over the holiday weekend. We enjoyed spending the weekend with him and my sister who has now also moved to the area, as well as their significant others.
