This Open Road

A season walking southbound on the Appalachian Trail

Category Archives: Massachusetts


The Big Question is Why?

Why do long-distance hikers do this? We simply walk all day. My alarm goes off, I wait until it’s not completely dark anymore, I get up and make coffee (I boil water and pour it over my instant coffee in my cup), and start stuffing things in their various stuff sacks. An hour later I’ve eaten, packed and am ready to walk, usually around 7:00 a.m. At least it feels that way now. In the early days, it felt like preparing for battle.

It takes me a while to really wake up and find my rhythm. The sun begins to shine in earnest, coming in low, then higher, between the trees, always to my left, from the east. In the evening, I often wish I hadn’t sent my visor home, as the sun begins to set on my right. As a southbounder entering fall, I’m following the rising and setting of the sun as the earth moves in favor of the Southern Hemisphere. The darkness comes a little bit earlier at the end of each day.

And I walk. Occasionally (sometimes more often), I wonder why I’m driven to do this. There are many in my tribe who heed this mysterious call to walk the Big Three: the AT, CDT and PCT. The Long Trail, Colorado Trail, Arizona Trail, and John Muir Trail also make a hiker’s heart beat a little faster. I really don’t have an answer. It’s meditation or natural medicine. It’s peace and beauty and silence and mystery. It’s also simply this, “The long brown path before me leading wherever I choose.”



The Appalachian Trail could wrap a person up in those trees, and the path, strewn with rocks, will trip you and spit you out without a second thought. It doesn’t care. It beckons, then knocks you down, then beckons you on again.

* * * * *

I continued walking out of Vermont and stepped into Massachusetts, the fourth state down the trail. The first major road gives you a choice: left to North Adams, hard scrabble and grit, abandoned red brick factories with a museum-of-modern-art appeal, or right to upscale Williamstown, home of Williams College and the Clark Art Institute, sushi restaurants and prep school students. Williamstown had a North Face store with canister fuel and I was out, so to Williamstown I went.

I love both towns for their unique characteristics. The Clark Art Institute has one of the best art collections I’ve ever seen. I didn’t have time to go there on this trip, but I’ve been two other times and highly recommend it.

Williams College, Williamstown, MA

Williams College, Williamstown, MA.


The AT heads up toward Mount Greylock through a neighborhood street between the two towns. Greylock is the highest point in Massachusetts and is marked with the Veterans War Memorial Tower.

Mount Greylock.

Mount Greylock.


Two days and some now-forgotten miles later, I entered Cheshire, MA. The trail goes right through town and passes by some beautiful old historic buildings. A few humble structures had been the previous sites of the post office, now with just simple signs stating, “Post Office 1888 – 1900” or some similar date. A modern brick building now houses the current post office.

I needed to buy some supplies in town and wandered into an old-fashioned general store, which dated back to 1844. Although contemporary in many ways, there were features of its original state. The floor was weathered hardwood. The shelves behind the counter were arranged like scenes of the store in Little House on the Prairie. The fluorescent lights, refrigerators and electrical gadgets represented a more recent era, but it was easy to look past these things and imagine a time when a horse and buggy would have been tied out front where the tractors were now situated. The elderly lady working behind the counter told me that her father-in-law bought the store in the 1930s and he had been the third owner.







The Cheshire Town Hall.


Nine miles later, I walked through Dalton, had lunch at a cafe and charged my phone. The residents of Dalton and Cheshire have seen thousands of hikers walk through their streets, and there is a welcoming feeling in these towns.

The next day, I stopped by another AT landmark, The Cookie Lady’s House. The Cookie Lady has been giving away homemade cookies for many years to any hiker that stops by. She and her husband live in this house, just 100 yards down a country road which crosses the trail. They also sell eggs, sodas and ice cream, and hikers can also tent in their yard with permission. I chatted with her for quite a while, signed the guest book and returned to the trail.




Upper Goose Pond Cabin is a place I had been looking forward to visiting while planning this trip. The cabin sits just up the hill from the pond and is looked after by a caretaker during the summer and early fall. There is no electricity or running water. There are bunks on the second floor, a fireplace and tables and chairs in the main room. Visitors can swim in the pond or take a canoe out.


During this visit, The Digger, Soynuts and Bud performed an original song they wrote. Soynuts is a one-man band, as he carries a backpacker guitar and a harmonica and plays both really well. (And naturally, The Digger carries that shovel as he hikes. We don’t know why… but if you’re ever in need of a shovel and The Digger is nearby, you’re in luck!)



Soynuts, Bud, Grits and Deja.


One of the many great aspects of hiking the trail again is getting to reconnect with friends I made on previous hikes. I met Flutterby during my 1998 thru-hike and although we never actually hiked together, by happy chance, we summited Katahdin on the same day. During this trip, as I got closer to Flutterby’s neck of the woods, she enthusiastically and generously became my own personal Trail Angel. I needed a place to land for a couple of days, to do my online work and she graciously invited me into her home to do this. It was perfect. I took a series of local shuttles from the trail to Great Barrington, where she met me, and then took me to dinner. We talked about backpacking and trail life and the friendships we’ve both made during our trips. At her house I took over her guest bedroom and a corner of her living room where I set up my portable office. Flutterby had to work the next day, but that night we enjoyed a home-cooked curry dinner she and her friend, Ryan, prepared. It was a great evening of talking, music and rest.


I was still in Flutterby’s area the next week, so we did a repeat of the previous week. This time she had to be away on a business trip, so Uma kept me company while I was at the house. I couldn’t thank Flutterby enough for her generous gift of friendship, her home and help during these two weeks.


Uma, trail angel cat.


Then, as this trail life dictates, the AT called me out again.




This happened here.


Late one afternoon, lost in thought, I looked up to see that I was about to leave Massachusetts behind and enter Connecticut. I’d walked 684 miles from Katahdin. These state lines were starting to come a little quicker. Next, Connecticut and New York.