Slackpacking Massachusetts: The Appalachian Trail's Best-Kept Secret

Posted: Tuesday, May 23, 2023

When I crossed the border from Connecticut into Massachusetts, the swelteringly hot Mid-Atlantic summer of 2022 finally relented, and I was greeted with cooler temperatures and the clearest springs I had seen since Virginia. This is easily some of the prettiest trail I’ve seen in a long time, I wrote in my journal.

I didn’t know it then, but the next 200 miles would be my favorite section of the entire Appalachian Trail. The next 90 miles through the Berkshire region were stunning, culminating with the 3,491 feet tall Mt. Greylock, the highest and most beautiful peak in Massachusetts.


Babbling creeks and cascading waterfalls lined by mossy boulders, evergreen forests and forgiving terrain that undulated at gentle slopes without punishing hiker knees, and wide views of the surrounding landscape offered sights and sounds I hadn’t seen in weeks. Since Pennsylvania, all the hikers and animals in these woods had been baking under the ever-present sun. The shimmering heat led to a strange hush along the trail, which was only punctuated by raspy-sounding cicada calls and even the occasional warning from a timber rattlesnake. Now, in the cooler, shady forest, I was hearing birdsong, frogs croaking in streams, and gurgling water running underneath it all.

No one had told me to look forward to Massachusetts when I was planning my thru hike. It never made the lists of “most scenic” destinations along the trail, alongside the likes of the Shenandoahs, the White Mountains in New Hampshire, and of course Maine. But, Massachusetts is one of the few sections I would hike again in a heartbeat. 

Here’s why:

The History

The Berkshires are not only a gorgeous part of the AT, they’re also rich in cultural history. This region was home to the Mohican people. They inhabited the Hudson River Valley for thousands of years before the arrival of the Europeans. The Muh-he-con-neok, the “People of the Waters That are Never Still” were then largely forced to uproot and move many times to their present land in Wisconsin, but their memory remains. Along the trail, I saw posted signs reminding hikers of this:

“You are traveling through the homelands of the Mohican people, the indigenous inhabitants of this land,” one sign nailed to a tree near the trail read. “Please respect this land during your journey.”

As you walk along this section of trail, unburdened by a heavy pack, you’ll have the energy and time to soak all of it in. If I could return to this section of the trail, I would hike it just as you would on our slackpacking trip: taking more time to be present and immerse yourself in the natural beauty  and  historical significance of this section of trail.

On a slackpacking trip, you hike the full length of the Massachusetts section of the AT, but return to comfortable lodging and a hot meal and shower each night:

Your lodging for this trip, the Villa Favorita, is also steeped in history as well. The home sits by the edge of a field with garden and blackberry patch and is surrounded by 25 acres of woods. It was built in 1918, upgraded to its current structure soon after by Clive Livingston Duval I (father of a Virginia Senator of the same name), and later became the home of royalty, Prince and Princess Sapieha, after they escaped Eastern Europe during WWII. 

Former residents kept their own horses here, and former pasture, equestrian fields and orchards have now evolved into wild meadows, cultivated blackberry and raspberry fields, and walking pathways through forests of pine, maple and fruit trees.

The Scenery

The border of Massachusetts begins on the slopes of Bear Mountain. Compared to the mid-Atlantic and Connecticut, the climbs in Massachusetts are longer and generally, well-graded. You’ll enjoy a good mix of easy terrain, and some challenging terrain as you climb Mount Everett (a rocky peak with long-range views) and Mt. Greylock. 

As you begin your slackpacking trip with us, just past the border, you will walk onto the trail at the Housatonic River trailhead near Great Barrington, MA. As you hike up the first climbs of the trip, you will be greeted by fantastic views of the South Taconic Range, including Mounts Bear, Race, Everett, and Bushnell. Along the trail, you enjoy blooming magnolias, poppies, milkweed, and wild indigo, and catch sights of orange spotted newts, wild turkey, deer, and woodchucks.

Insider tip: Before we end our first day at the Route 23 crossing, you walk near a feature called the Ice Gulch, where the AT winds alongside the western edge of a deep ravine within a dense conifer forest. The shade and depth creates conditions that may keep snow at the bottom of the gulch until the middle of summer, but on hot days, it’s a great place to enjoy some cool shade and interesting scenery. 

We’ll begin each day of our trip where we left off the previous day, so you will complete an uninterrupted section of the Appalachian Trail. You gain and lose just around 2,000 feet of elevation a day, and hike anywhere from 8 to 14 miles each day.

One of my favorite stops, which you see as well, includes the town of Dalton, which is an officially recognized “Appalachian Trail Community.” As a thru-hiker, it was a relief to walk into a town knowing that I was welcome there. 

You will end your slackpacking trip with us by climbing the formidable Mt. Greylock. But don’t worry–while it is the highest peak in Massachusetts, the trail is nicely graded. And by then, you will have your trail legs under you! 

From the summit of Mt. Greylock, you will be able to see four different states and five mountain ranges. My favorite part of this summit is the gorgeous boreal forest. As Massachusetts’ only subalpine environment, it’s a rare and beautiful place. As you hike up, you pass the southern edge of a tiny pond, where an old cabin sits nestled among the trees. It’s easy to miss, so keep an eye out for it! 

Slackpacking trips combine the best of both worlds: a long day hiking in the backcountry, followed by a hot meal and shower so you can relax and unwind at the end of each day. Join us on Slackpacking Massachusetts!

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