While it’s true New York City’s Metro-North let’s riders off on right on the Appalachian Trail, another section of trail that’s perfect for hikers in New York City, and particularly hikers in the city without a car, is the Massachusetts section. Working as a special education teacher gives me the luxury of summer breaks, so on my first two week break, I set out to complete this section with my brother J-Dub who thru-hiked the trail in 2012. My brother pick me up at the Wassaic Metro-North stop, but car-less hikers could take a Peter Pan bus line that makes a stop in Great Barrington, providing easy access to the trail.

My family is from Pittsfield, and my brother is currently living there, helping my Uncle with the clean-up and sale of an old family home. Once in Pittsfield we were able to take the BRTA Bus, or Bbus, a relatively new public transit initiative that takes riders all over the Berkshires. My brother and I rode the One bus, then transferred at North Adams to the Three bus which dropped us off about .3 miles from the Pine Cobble Trailhead.

The Pine Cobble is a blue blazed AT access trail in Williamstown, MA maintained by the Williamstown Rural Lands Foundation. It’s a steep 2.1 mile [1]ascent that interests with the AT 1.3 miles from the Vermont border. We took a quick break on the Pine Cobble rock formation itself which offers a view of the valley below, the went the 1.3 up to the Vermont border in order to turn around and begin our southbound section hike.

MA Section Hike VT Border

VT border! You can tell it’s day 1 because I still look clean. [photo by Jonathan Welch]

The first day we traveled 10.3 miles, but only 6.9 miles of those were trail miles moving us southbound, the other 3.4 mi included the Pine Cobble Trail and backtracking to the Vermont border. We found a campsite at an amazing overlook of Williamstown and the valley by the Mt. Prospect Trail turnoff where we could hear the long whistle of evening trains about to enter mountain tunnels. We had begun our climb of the Greylock ridgeline, comprised of Mt. Prospect, Mt. Williams, and Mt. Greylock, and were exhausted. One of the biggest challenges in section hiking is that it’s hard to get trail legs, the going is slow and, since we had opted to start in the most challenging section of the state, I was ready for sleep.

Our second day began with the climb up Mt. Williams and summiting Mt. Greylock itself. The ridgeline on the north side was incredibly steep and I was feeling it in my legs, however, it was nice to know that our biggest climb, until Mt. Everet at the end, was now behind us. Getting on top of Greylock is always exhilarating. I’ve been up to the mountain many times and recently summited it up the local Thunderbolt Trail, but making it up the entire length of that ridgeline and looking into the Berkshires and beyond was an amazing feeling of accomplishment. While we still had about 79 miles ago, according to the sign in Bascom Lodge, I savored this tiny victory with a tuna wrap sandwich. We proceeded down Greylock and crossed the smaller summit of Saddleball, Herman Melville’s inspiration for Moby Dick. In Pittsfield you can look out the Window of Melville’s study at Arrowhead and see Greylock with Saddelball’s hump rising off the side of it, like a large whale, the view is especially on a gray winter day. We went 11.7 miles, stopping that night in Cheshire, to buy soft serve ice cream from a roadside stand, and stay at hiker hostel that St. Mary’s church offers free of charge.

MA Section hike Cheese Wheel

Monument to a cheese press in Cheshire, in case you were wondering Cheshire is not the birthplace of the cheese press or even the modern cheese press, but they still have this monument.

With a good night’s sleep and no time spent breaking camp we quickly made it to the Cobbles and stopped for a breakfast break admiring the view. The Cobbles overlook the town of Cheshire and from that vantage we were able to see the full expanse of Greylock and its ridge, standing guard over Cheshire Lake and the small parcels of farmland in the valley. I remember watching a boat slowly make its way across Cheshire Lake, seeing the entirety of its wake spread across the water in smaller and smaller waves reaching both sides of the shore. We pressed on into Dalton and stopped for lunch at Angelina’s Subs, my favorite sandwich place in the Berkshires. I remember going here as a kid and I make a point to go here whenever I come back to Pittsfield. My absolute favorite sandwich is a triple cheeseburger sub, but we were stopping at the height of the afternoon, so I opted for a classic ham and Swiss rather than chance a hot grinder. We stopped that night at the Kay Wood shelter, using one of the splendid tent sites available, making it an 11.8 mile day for us.

All hike we had been hearing about Upper Goose Pond Cabin with fables a of pancake breakfast with coffee in the mornings. We decided to set out and see if the rumors were true or just a tall tale grown larger down the trail. Kay Wood Shelter to Upper Goose Pond Cabin would be a 17 mile day for us, our biggest yet, but having done Greylock, the toughest terrain of the state, the rolling hills along the 17 miles were pretty doable. This isn’t to say it was incredibly tiring, especially with all the roots and rocks jutting out to test our ankle strength, but it felt nice to push ourselves on the section hike. When we made it Upper Goose Pond Cabin there were twenty-nine hikers there! The cabin and camping spots were all taken so we had to set up down by the pond’s canoe launch at an impromptu site. The spot was admittedly beautiful, but buggy as hell.

MA Section hike Upper Goose

In the morning there were in fact pancakes and coffee! Eating with the new hostel caretakers, they cycle through weekly shifts, I learned that they were from Washington Heights, the neighborhood right below my new home of Inwood. The pervasiveness of New York City is astounding, even here, in a cabin in the Massachusetts wilderness, I was talking about the neighborhoods of upper-Manhattan and discussing the politics of the NYC Park’s Department. With full stomachs and caffeine (first time in five days) we set off for another big day, shooting for the Mt. Wilcox South Shelter 16 miles away.

This hike led us through Tyringham which, with its rolling pasture lands and miles of fields walking reminded my brother of Ireland, a comparison that felt pretty spot on to me. At Jerusalem Road a little stand had been set up by farm kids selling fruit snacks, drinks, eggs, and granola bars. The stand also offered a power strip to charge phones which was it’s own kind of trail magic. My brother and I stopped here to let our phones charge while we restocked on snacks and enjoyed cold Gatorades under the shade of an old oak tree before going up the Tyringham Cobbles and onto Mt. Wilcox. The weather was beginning to turn and the wear of two big days was taking its toll, so we decided to stop in at the Mt. Wilcox North Shelter instead, but once we got down to the shelter the water source turned out to be dry. Massachusetts is in the midst of drought, so water had already been a concern on the hike as springs and streams along the path had proven unreliable, however this was the first dry shelter source we had encountered.

MA Section Hike Water Break

Water break in a dry stream bed. [photo by Jonathan Welch]

We needed a shelter with water, so we packed up and pushed the 1.9 miles to Mt. Wilcox South Shelter, our original target. This shelter had a little spring along it’s entrance trail that wasn’t flowing too well, but was the best source we had on the ridge. This site has two shelters, the original one built by the Civilian Conservation Corps during the Great Depression and a new one constructed in 2007. We went with the new one and slept in the shelter rather than tent with the threat of rain.

The much needed rain didn’t arrive. We had a few small bursts late in the night, but nothing noteworthy, just enough to leave the mountain entrenched in fog, giving the forest a Tolkien-like quality. While that rain system was a dud, we heard rumors of a thunderstorm in the forecast for the day. Having just trekked two big days, and with no desire to hike through lightening, we took a Nero, hiking 5.3 miles to the Tom Leonard Shelter. Despite the short day, the terrain was rocky and slick from the light rain the night before making it slow going. The water at the shelter was a nice creek, but getting to it was a steep .25 miles downhill which of course meant .25 back up.  However, while we were resting in the day a Mass. Department of Conservation and Recreation (DCR) trail crew came through, having just finished a re-routing south of the shelter they were now tasked with building switchbacks into the water trail. Along with this, they were debating the best methods to keep porcupines out the shelter. The Tom Leonard shelter was pock-marked with porcupine bites, from the floor all the way up the ladders into the crow’s nest section. While this is certainly a serious concern, I couldn’t help but find it comical how much havoc and consternation porcupines caused. Ultimately it seemed that a kind of spring loaded, tin step would be the best plan of attack and I’d be curious to one day hike back to that shelter and see what’s become of the porcupine menace.

Surviving a porcupine free night and getting a thunderstorm only late at night, we woke up rested, refreshed, and ready to get moving. By this point we had a few blisters and bruises, but thankfully the trail ahead leveled out rather quickly and we were walking through Eggermont farmland for 10 miles on our way to the Appalachian Trail Conservancy’s (ATC) Kellogg Conservation Center. The people at the ATC office were incredibly kind to us, allowing us to fill up water, charge our phones, and pass the heat of the afternoon on a shaded, outdoor, patio area. In case you haven’t noticed the pattern, breaking in the afternoon was an important tactic for our summer hike. We’d often find a shelter or shady place, preferably with water, and lunch for an hour or two letting the afternoon pass in order to avoid the heat and keep ourselves hydrated.

MA Section Hike Shays Rebellion

Monument to Shay’s Rebellion in Eggermont [photo by Jonathan Welch]

Getting started back up in the late afternoon, we bumped into a couple of Southbound hikers we had first met at Upper Goose Pond Cabin. This was their first time hiking and they asked if they could join us, they had twix and potato chips so we agreed and set off as a four hiker caravan up Jug End and onwards to the summit of Mt. Everet. While the water here, as with much of the trail, was sparse a trail angel left a cache of gallons and gallons of water in the Guilder Pond picnic area, intersecting the trail before it ascends Mt. Everet, allowing us to fill up before our big climb. We contemplated pushing on as we descended Everet and came to the Race Brook Campsite, but the 6.2 miles from the ATC’s office made it a 16.2mile day for my brother and I and the two hikers with us were beat from the climb, so we decided to play it safe and camp here, still keeping ourselves within striking range of the Connecticut border.

Day Eight had us positioned 4.2 miles from Sawmill Creek, the MA/CT border. The only real obstacle left was Mt. Race, which didn’t feel like an obstacle at all while summiting. Unlike Everet which is shrouded in trees and the remains of an old fire tower, Mt. Race offers a panoramic view of the Housatonic Valley and surrounding terrain, from Greylock in the distant north, to Bear Mountain and beyond into New York looking South. As majestic as Greylock is, the parking lot and rabid tourism admittedly detracts from the emotional impact of its vista, Mt. Race has none of the glamour and sets hikers on perilous, but beautiful edge walks along its rocky summit.

MA Section Hike Mt. Race Summit

Summit of Mt. Race [photo by Jonathan Welch]

Coming down from Mt. Race we quickly crossed Sawmill Creek and touched the Connecticut border. While my brother completed a thru-hike in 2012, I’m adding another 91miles onto the 300+ (look up) I’ve already done. While this was certainly a satisfying, personal accomplishment, now J-Dub and I had to double back, climbing Mt. Race again and returning to Race Brook Campsite in order to follow the blue blazed Race Brook Falls trail two miles down to US 41 and our ride home. Like the Pine Cobble, Race Brook Falls trail is a steep access trail, but it’s broken up by a gorgeous waterfall which was running even in the midst of the state’s drought.

While J-Dub and I have family and friends in the area, for the hike without access to a car, it wouldn’t be hard to double back to US 7 and go into Great Barrington. In Great Barrington there take the BRTA Bus anywhere in the Berkshires or even take the Peter Ban bus right back to New York City, though they might want to stop in the hostel there to shower and do laundry first.

The mountains of Western Massachusetts offer their own kind of magic, J.K. Rowling even set a story about an American wizardry school on Mt. Greylock, from old mountain oaks to thick patches of dark pines. This state has so much more to offer visitors than James Taylor concerts at Tanglewood and a famous Stockbridge Inn. For hikers, the terrain is a nice variation of challenge, from Greylock, Everet, and Race Mountains, to the rolling idyllic strolls through the pastures of Tyringham and Eggermont. So if you’re in the city and itching to get out on a trail, then buy a bus ticket, grab a guide, and see what Western Massachusetts has in store for you!


[1] Mileage based on the ATC’s guide to Massachusetts and Connecticut edited by Sue Spring 13th edition

4 thoughts on “Appalachian Trail Section Hike: Massachusetts

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