Tales from The Trail: The ‘Cookie Lady’ of the Appalachian Trail

There are always lessons to be learned on the trail, and they aren’t always related to building a campfire, setting up a tent, or leaving your campsite cleaner than when you arrived.

Some of these are life lessons that fall in the category of treating others as you would like to be treated and adhering to the principles of human kindness. Take, for instance, an experience I had while hiking along a stretch of the 2,200-mile Appalachian National Scenic Trail, or simply, the AT.

For days, I kept running across hikers along a Massachusetts section of the AT, and often during our short conversations, they would tell me stories about a “Cookie Lady” on up the trail. It got to the point where it seemed every other hiker told me, “You just gotta stop at the “Cookie Lady’s” house. Best cookies ever!”

Then these thoughtful fellow travelers would painstakingly give me directions to a blueberry farm just off the trail in western Massachusetts. It seems Marilyn Wiley, along with her husband Roy, owned the farm in rural Washington, Mass., that had several outbuildings, including one with what appeared to be storing a small airplane.

And since buying the place back in 1983, Marilyn Wiley would walk out front and hand out her scrumptious cookies to blueberry pickers and hikers passing her farm on the Appalachian Trail.

A few days into that part of my trek, I found myself approaching a country road in western Massachusetts in search of the famed “Cookie Lady.” I told my dog Henry that there might even be a treat for him at the “Cookie Lady’s” house.

As I pressed on, I spotted hikers coming my way, their heads somewhat down and frowns on their faces. Each of them looked up long enough to tell me that the “Cookie Lady” isn’t home and there’ll be no cookies today.

The news gave me pause, but I decided to keep walking toward the famed blueberry farm and its more famous baker of cookies. When I arrived at the house, I saw Roy Wiley standing in the driveway. He was in the process of turning a couple of hikers away.

Spotting the airplane through an opening of an outbuilding, I asked what kind of plane it was. He looked me up and down and said, “You want to see the plane?”

“Sure,” I said.

As he was showing me around the aircraft, I noticed the Wiley’s had a dog. And since I needed dog food for Henry, I asked Roy if I could purchase a little from him. He told me there was no need to pay, and to go ahead and load up some bags and grab a couple of bones while I was at it.

I was appreciative of his kindness and I told him so. After a few more questions about his farm, I bid Roy and dog goodbye. Then, as I was putting on my backpack and getting ready to head back to the trail, over my shoulder I heard my Roy ask if I wanted some cookies.

I told him I had heard there were no cookies today. He said there were no cookies today for those who came only looking for cookies and had no interest in the folks who were making the cookies.

Roy then went inside, returning a moment later with the most delicious cookies, as well as his wife, Marilyn, the famous “Cookie Lady,” who was grinning from ear to ear.

I realized right there that it was my curiosity that led me to their farm. The decision to continue to hike to there — even though there was no guarantee of cookies — and then asking questions, being kind, and enjoying the human connection, was all that mattered.

I heard later that the Wiley’s sold the farm and moved, and that Roy passed away in 2019 at the age of 88. The new owners — the Sangree family — renamed the property “Blueberry Hill by the Appalachian Trail.” And they have indicated in messages posted online that they plan to continue the “Cookie Lady’s” tradition started by Marilyn Wiley.

I will never forget the hospitality of that wonderful Appalachian couple. Nor will I forget how yummy those cookies were on the trail.

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About the Author: Stephen Mullaney is the Director of School Partnerships at The National Center for Outdoor & Adventure Education (NCOAE). He has worked domestically and internationally with schools, organizations, and wilderness programs. His classrooms have ranged from dilapidated trailers at overcrowded, underfunded schools to the Himalayan mountains and everything imaginable in between. His past students include gang members/prisoners, education majors, college and university professors, and pioneers in the field out outdoor and adventure-based experiential education. Stephen’s philosophy is to focus on the development of positive working and learning environments. He brings more than a quarter of a century of education experience and understanding of human nature to any organization, whether it is an education institution or a private company. His writing has appeared in adventure sports/education journals, magazines and on the web. Stephen prefers to arrive by bicycle and sit in the dirt.