Slackpacking the Berkshires: A Week on the AT in Massachusetts

Posted: Monday, July 13, 2026

A couple of weeks ago, our group wrapped up a week on the Appalachian Trail in Massachusetts. It's hard to put a week like that into words, but we are trying to share taste of what it was like. Here's a look back at the adventure.

 

 

Sunday: Cookie Ladies and Lady Slippers — Country Rd to Dalton, MA (13.8 mi)

The trail greeted the group with open arms, staying AT flat for the first half of the day. Spirits were lifted by a stop at the cookie lady, and the group meandered on, eager to see what was ahead and get to know their new trail friends. The first flower of the trip was identified along the way—a Lady Slipper! Halfway through the day came the first real climb, up to Warner Hill, before the group cruised down into the quaint town of Dalton.

 

 

 

Monday: Tackling PUDs and the Climb to Tyringham Cobble (12.4 mi)

Day two brought the "famed" hardest day of the trip, and the group took it in stride—PUDs (pointless ups & downs) and all. Lunch was by a lovely brook, wildlife sightings were plentiful (the chipmunks seemed especially thrilled), and a snake made a brief trailside appearance until Jen bravely relocated it. The real challenge came with a late climb up to Tyringham Cobble, which was rewarded with a shaded bench offering sweeping New England views.

 

 

Tuesday: Crossing the Mass Turnpike on the Long Push to Beckett Mountain (14 mi)

Tuesday opened with a daunting uphill, tackled early while energy was high. A flat stretch led to a beautiful pond before lunch, and crossing the Mass Turnpike brought cheers from passing cars. Some hikers took Jaime's offered takeout option to rest up for the days ahead, while the rest pushed on up Beckett Mountain and rambled through Massachusetts forest for the afternoon. Everyone was glad to see Jaime and the van waiting at day's end after 14 solid miles.

 

 

 

Wednesday: A "Level 6" Climb to the Ice Gulch (10.2 mi)

The day began with a lovely flat walk through forest and meadow—almost too lovely for trail life. That gentle start gave way to what guide Jess rightfully called a "level 6" ascent, and the group pushed through with determination to a well-earned lunch break at the ledges, a perfect photo-shoot spot. The trail continued on to the ice gulch, a lush, rocky ravine that seemed to appear out of nowhere. Trail angel Jaime greeted everyone at day's end with homemade limeade and unbeatably refreshing watermelon.

 

 

Thursday: Reservoir Views and Farm-Fresh Ice Cream Near Cheshire (8.7 mi)

The promise of a lower-mileage day was a welcome reprieve. One climb of the day proved mercifully short, and the group carried on to the cobble for lunch, where the forest seemed to open up just for them. Views over the Cheshire Reservoir, another epic photo shoot, and perfect relaxing rocks rounded out the break. The day ended with a surprise stop at High Lawn Farm for farm-fresh ice cream, courtesy of some very cute Jersey cows.

 

 

Friday: A Sunrise Summit at Mt. Greylock — The Final Descent (8.2 mi)

For the final day, the group switched direction, starting at the summit of Greylock and heading south to try to beat the heat and clouds. The summit view didn't quite cooperate, but good mileage was covered before the heat and humidity set in. After a last lunch at the final shelter, the group pushed for a strong finish, and by the time they were descending Greylock's mountain road in the rising heat, everyone agreed hiking south had been the right call.

AGC traveler Anne summed up the week best: 8 strong women, 7 weird bathrooms, 6 wildlife sightings (mostly for Lori's benefit), 5 liters of fluid a day, 4 meals a day, 3 talented guides, 2 trekking poles, and 1 famous pair of pink panties.

It was a joyful week, full of support and encouragement, as this group challenged themselves and hiked nearly 70 miles along the Massachusetts section of the Appalachian Trail— proof that there's nothing quite like tackling the trail together.

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