3 Days in Western Massachusetts

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Pittsfield & Great Barrington, MA | April 2023

Our time in Western Massachusetts went by quickly. We spent some time with Curtis’ brother, going out for meals, walking around Great Barrington, and visiting him at work. When we weren’t with him, we spent some time decompressing after our eventful month, relaxing in preparation for what was to come, and going for a few easy adventures in the area.

Beartown State Forest

On our first full day in Massachusetts, we went for a short hike up the Lookout Mountain Trail in Beartown State Forest. This was the first hike we had done in the Northeast this month where we truly didn’t need microspikes! Of course, that meant the bugs were starting to appear. This trail was .6 miles long round trip, with switchbacks going up and ending up at a clear view to the West. We sat at the picnic table here for a while and enjoyed the view, and watching the hawks flying overhead.

Wahconah Falls

The next day, we drove East of Pittsfield to go for a short hike to Wahconah Falls. It turned out to be even shorter than we thought, maybe just a tenth of a mile from the parking lot to the falls. At least it was easy enough for Charlotte, and there was plenty of room for her to sniff around without having to go out on the rocks or be near the other people there. After a few minutes here, we searched Google maps for another short hike, and found one a few miles Southwest of where we were.

Old Mill Trail

After leaving Wahconah Falls, we drove to the Old Mill Trail along the East Branch of the Housatonic River. This one seemed easy enough for Charlotte as it was a flat, wide, and well shaded trail. She really seemed to enjoy it, so much so that we made it to the first road crossing before turning around. We enjoyed reading about and seeing little bits of history scattered around, like the car in the above image.

Laura Hill

On Saturday morning, it was time to check out of the Airbnb and begin our drive South. We made plans to meet with Curtis’ brother for lunch, so on our way we stopped to go for one more walk. This morning, we were attempting the Laura/Lara Tower Trail in Stockbridge, MA. This trail was 2 miles long and had a steady uphill climb the whole way up. There were roots and rocks in the path, but with our guidance Charlotte navigated it so well, both up and down. It may have taken us over 2 hours to hike the whole thing, but we were able to finish it and that’s what counts! We crossed paths with a family with a young daughter multiple times and laughed with them about how it’s not so different hiking with a child than it is with a blind dog. They couldn’t tell that Char was blind before we told them, and were impressed with how well she was doing.

After our hike, we met with Curtis’ brother at a Greek restaurant for lunch in Great Barrington before parting ways and continuing our drive South.

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