A section of the Appalachian Trail near the Cobble. 

Sherry Cook set up Thursday on the side of the Appalachian Trail near its intersection with Jerusalem Road in Tyringham, where she provided hikers with cold drinks and snacks.

Greta Jochem pauses on her way north on the Appalachian Trail. 

The stand selling snacks for hikers on the Appalachian Trail, on Jerusalem Road in Tyringham, is well-equipped.

This stand sells Pop-Tarts, Gatorade and other snacks for hikers on the Appalachian Trail, on Jerusalem Road in Tyringham.

Debbie Cranwell is a member of a remarkable community of people that helps lift daily burdens for Appalachian Trail hikers. Literally. Cranwell gives people rides. 

My parting gift from Sherry Cook.

The trail's route through Massachusetts reminds residents of its long reach, including through this sign in Great Barrington. 

This road sign, over the Mass Pike, is perhaps the most visible reminder of the trail's passage through Massachusetts. 

A section of the Appalachian Trail near the Cobble. 

Berkshire Eagle reporter Greta Jochem is providing dispatches from a trip north on the Massachusetts section of the Appalachian Trail. She hit the trail Monday, Aug. 1, at the Connecticut line. One of the first hikers she encountered told her: “Backpacking, you get to see a lot of the world you normally wouldn’t see.” Jochem's journey, and reports from the field, continue this week.

I came upon Sherry Cook on a quiet stretch of Jerusalem Road in Tyringham, where she was setting up a tent next to her parked car. The open trunk revealed donuts, a cooler and snacks.

She had driven from North Reading, in northeastern Massachusetts, to offer hikers food and cool drinks and to meet up with her 26-year-old daughter, who is hiking the trail and about 10 miles south.

In 2019, Cook, known on the trail as TeeBeeDee, hiked the whole AT. She started hiking in her 20s, and then heard about this route.

"You can get on a trail in Georgia and walk all the way to Maine?" she recalled thinking. She wondered if she could do it, and decades later, when her son went to college, she decided to try. She turned 57 on the trail and summited Mount Katahdin in Maine with a group of hikers all above age 40.

"As a collective we called ourselves the grey walkers," she said.

Sherry Cook set up Thursday on the side of the Appalachian Trail near its intersection with Jerusalem Road in Tyringham, where she provided hikers with cold drinks and snacks.

Before she left on her hike, she read a lot about it. One book said if you have lost faith in humanity, then hike the Appalachian Trail. "My experience is that's a truth." She saw kindness from strangers, like when she hitchhiked — "I really stunk and they put me in their car," she said.

While hiking, she met people she would not have normally connect with. "I'm a white-haired suburban mom," she said. On the trail, she'd find herself sitting around a fire with a tattooed 20-something. People have lots of reasons for going on the expedition, but, in her view, all have one thing in common: "Some crazy thing makes you think this is a good way to spend five months."

"It made me more open to strangers," she said.

Getting up from a camp chair, about 34 miles into my 90-mile trip along the trail's Massachusetts section, I felt self-conscious of the smell and sweat I was leaving behind — and apologized. "Embrace the stink, sister," she said, offering me a bag of candy for the road. I happily accepted.

My parting gift from Sherry Cook.

As I walked across the street back to the trail, I saw two other hikers reach TeeBeeDee.

"I'm Bed," one said. "And I'm Breakfast," the other said. "And together we're Bed and Breakfast."

I expected to feel alone, but so far that hasn’t been the case. Though I am mostly walking by myself, there’s a steady stream of people on and around the trail. Sometimes we exchange a hello and "happy trails." If it aligns during a break, we stop and chat.

The trail's route through Massachusetts reminds residents of its long reach, including through this sign in Great Barrington. 

A few days in, my "trail legs" not quite in place, I was walking north about 10 miles a day in the heat, passing ponds and over streams. Through grassy fields. Through Beartown State Forest. Hiking up and down inclines in the trees.

About a mile down the trail after crossing Main Road, I found Debbie Cranwell sitting in the shade with water, bananas, apples and ramen noodles. For the past few years, she, like others, has been coming here to support hikers.

She goes by "Wheels," and it is fitting. She offers, for free, to drive hikers' backpacks several miles down the road and then meet them there, just to ease their loads. She will also give rides to people to Lee, several miles away. "It's a long haul," she said.

Debbie Cranwell is a member of a remarkable community of people that helps lift daily burdens for Appalachian Trail hikers. Literally. Cranwell gives people rides. 

Though Wheels lives nearby in Lee and had driven past spots where the trail crosses the road, she did not know a lot about it until a few years ago when she started watching Craig Mains, a hiker who makes regular YouTube videos. She started hiking parts of the trail and helping hikers. Since then, she's gotten good at spotting them. Once, when she was in the grocery store, she saw a guy who looked like a hiker and asked if he needed a ride back to the trail. “How did you know?" he asked.

After refilling my water bottle from a jug she had, Cranwell warned me there was a bit of a climb up ahead on the way to Upper Goose Pond — several miles away.

I moved slowly, and two hikers doing the whole trail passed me, and told me, in the nicest way possible, I was doing great for not having my "trail legs" yet.

I was sweating, as usual, as I walked uphill in the heat. What kept me moving was thinking about jumping into Upper Goose Pond.

Greta Jochem pauses on her way north on the Appalachian Trail. 

To keep my news flowing, in text messages and photos to an editor at The Eagle, I hit the trail with gear that lets me charge my cell phone. Last week, even that was running low, so the Eagle mother ship sent a co-worker, Matt Martinez, to bring me a fresh battery pack. We picked a spot where the trail crosses a main road.

By that time, I was low on power, so when he got turned around, we had no way to talk. I didn’t mind taking a break. 

I was surprised to see Matt get out of a car driven by a man I didn’t know. Matt had gotten lost and began to search the trail for me. He managed to enlist help from a family from Georgia who, somehow, knew the way. They offered him a ride to our rendezvous point. 

Have you seen a bear? I got that question from a hiker walking fast in the opposite direction.

I come on a sign on the trail near Beartown Mountain Road that alerts hikers that a bear and cubs have spotted this summer. Miles later, I arrive at the trail's Shaker campsite, and find another bear warning.

I have seen more bears in my old neighborhood in Northampton — three — than I have when hiking — just one, years ago. Still, when two other hikers show up and set up their tents, I'm relieved to think I won't be alone if a bear does visit.

Erin Wolf, 41, had been hiking with Camilla Orr, 39, for the past 100 miles or so. “I like the physical challenge," Wolf told me. She's known up here as Lone Wolf. 

The sun was going down at the Shaker campsite, about 42 miles north of the Connecticut line. We talked at a picnic table over dinner. Also, it's freeing to be outside, she told me. Setting your schedule. Being away from the rhythm out there in the non-trail world.

This is the third long-distance trail she's hiked. Wolf took on the Pacific Crest Trail, a more than 2,600-mile route on the west coast. Also the Continental Divide Trail, a trek from the U.S. border with Mexico to Canada. It's satisfying for her to see how strong she can be.

One of the more stressful parts: Money, Wolf said. “Things are costing more — that's been a big challenge for me.”

It's also stressful, she says, to think about coming home and having "no room to spare" in her bank account and knowing she needs to find another job. Before setting out on this hike, she worked in crisis management.

Being present is also a challenge. She finds her thoughts pulled into the past and future, replaying conversations. "It's work to be present,” she said.

It's hard not to investigate every corner of your mind on a long-distance hike, Orr adds. She too hiked the Pacific Crest Trail. “The PCT didn't solve my problems,” she said, warming ramen noodles on a camp stove. “It gave me time to work out some things.”

This stand sells Pop-Tarts, Gatorade and other snacks for hikers on the Appalachian Trail, on Jerusalem Road in Tyringham.

The stand selling snacks for hikers on the Appalachian Trail, on Jerusalem Road in Tyringham, is well-equipped.

Out of nowhere: A small trail stand comes into view selling Pop-Tarts, Gatorade and other snacks for hikers.

It's all on the honor system. 

Sitting on the side of the trail, three young hikers are talking about their plans to get a ride into Great Barrington to re-supply.

I asked one of them, Will Leslie, about his trip. He told me he's been preparing for years. "I've been saving since I was 16," he said. Maybe that explains his trail name: Psyched. Growing up in Tennessee near the Great Smoky Mountains, he hiked a lot and prepared for this more than 2,000-mile trek.

"Everyone is willing to give you the skin off their back to get through," he said

The trio met while hiking and have been traveling together. "It all happened naturally out here," said Logan Giroux (Yogi). "Now we're just really good friends," added Peter Miler, 24.

Miler, who goes by Flapjack, was working in a Japanese restaurant in Portland, Maine, and looking for a break. He has hiked in Baxter State Park, which includes Mount Katahdin, the end of the trail. "I'd see people finish their thru-hike, " he said. "Just the wild emotions they experience up there."

This road sign, over the Mass Pike, is perhaps the most visible reminder of the trail's passage through Massachusetts. 

Though determined to reach the end of the trail, they've also been having fun. A guy they met in Virginia bought them food and let them cool off in his pool.

"You can't predict the people you'll interact with," Flapjack said. "You can't script that."

A few miles later, some hikers saw these guys and greeted them. Word passed that they'd been interviewed by a journalist. News travels fast on the trail.

Greta Jochem can be reached at gjochem@berkshireeagle.com or 413-496-6272.

Greta Jochem, a Report for America Corps member, joined the Eagle in 2021. Previously, she was a reporter at the Daily Hampshire Gazette. She is also a member of the investigations team.

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