7/6 – Glen Brook shelter, MA to Sheffield, MA – Jess Treat hostel
7/7 – Sheffield, MA – Jess Treat hostel
7/8 – Stealth site below Shaker campsite
7/9 – Overmountain shelter
7/10 – Cheshire, MA
7/11 – Bascom Lodge, Mt. Greylock
7/12 – Williamstown, MA
Last “week” I had just entered Massachusetts – my 11th state – and crossed the 1500-mile mark. This week covers my time there and ends at the MA-Vermont border. If there’s a theme to this week it’s simply – enjoying the hike again and being grateful for getting over my emotional low in New York.
The beautiful (generally rock-free) trails and exceptional trail maintenance continued after I entered Massachusetts. The day I left Connecticut I put in a tough day with four climbs (which remains one of my favorite hiking days of the entire trip) to avoid doing Mt. Everett (the first “mountain” in Massachusetts) in the rain because of the reputed steep, rocky descent.
The rain that was forecasted came the next morning, but fortunately after I broke camp (so I didn’t have to pack a wet tent). What I didn’t know was that descending to the trailhead that morning at Sheffield/Great Barrington (to pickup resupply) I would have a significant amount of rock ridges and ledges – which would be a typical/modest hiking challenge, but in the rain, a different equation.
After an hour of hiking I started down Bushnell Mountain and the sky opened up. Sunshine & Summer Breeze (and their dog) were hiking with me as the trails turned to streams and the rocks became wet (and as thundered sounded above). These were the conditions I have dreaded (and highlighted in My Banana Pudding Moment). While very challenging here, the rocks were not as steep as my concerns back in New York or as recently as the day before (Bear Mountain in Connecticut and Mt. Everett as I entered Massachusetts).
The descent was difficult, but with extra caution (read: very slow pace) I worked my way down unscathed. This required constantly looking for footholds on the rocks that were not angled or smooth, preferring dirt and roots over rocks, finding alternative routes down ledges, placing poles out in front to ease myself down, using trees to help balance while descending, stepping down backwards at times, and tossing poles down the slope when both hands were required. (I did watch a hiker in front of me slip and slide 15 feet down one of the ridges.) This went on for almost two hours. It was not as difficult as some areas where we’ve been and definitely not as tough as we’ll see in the White Mountains of New Hampshire and southern Maine, but still some good practice and confidence-building experience.
After that descent from Bushnell and Jug End (which would have offered some good views in better weather) the rain stopped and the hiking became quite easy – both good trails and little grade – passing through fields, swamp, conifer forest and bog, but featuring the worst mosquitos of the entire trip.
I had a nice visit, resupply and rest day with Jess Treat who welcomes hikers into her home in Sheffield. Then I was off again to finish Massachusetts and keep heading north. Despite my “banana pudding moment,” the visit with family, the wonderful hiking trails, another good rest, and the heat finally dissipating helped put me in a great frame of mind.
The hiking continued to be enjoyable. I was able to enjoy interesting beaver pond, some beautiful lakes, views out over the Berkshires, and some historical points, like a stone wall remaining from an old Shaker village. I was looking forward to seeing much of the trail I had done in a “shakedown” hike in 2016, but it just didn’t look the same. I eventually figured out that even since 2016 part of the AT here had been rerouted. I did run into my first southbound hiker who started at Mt. Katahdin. I walked through the towns of Dalton and Cheshire (tented in a church yard) and really noted how much hotter it was on the streets and sidewalks and in the exposed sun, as opposed to the woods and the “long green tunnel.”
Late in the state I climbed its highest point – Mt. Greylock, which holds a special place in my hiking life. I climbed Greylock in 1974, shortly after I learned there was such a thing as the Appalachian Trail. And then again in 2026 as part of my shakedown hike.
The views from that summit this third trip up were exceptional and I stayed in the hostel/lodge at the mountaintop.
I finished Massachusetts by descending from Greylock, staying in Williamstown to pickup a resupply box from Cheryl, and then hiking north another 4 or 5 miles to the Vermont border and the start of the Long Trail (a 270-mile trail from the MA/VT border to Vermont’s border with Canada, which was the country’s first long hiking trail and the inspiration for the Appalachian Trail).
I also met “Hawk” (who was starting his “thru-hike” of the Long Trail) as I was leaving Massachusetts. He would hike with me the next week (the Long Trail and the Appalachian Trail run concurrently for the first 100 miles of the Long Trail) as I continued to head north through Vermont on my way to Mt. Katahdin.
Last modified: July 25, 2018