Stockbridge to Boston


John and I were talking about striking out on your own. He mentioned how he, in his twenties, went out and built his own house, with no previous building experience. I told him how it’s a good feeling to live life independently, just doing your own thing, but sometimes it’s lonely and scary. I mentioned that one of the hardest things is the fear of not always knowing what’s ahead and the uncertainty of whether or not I can handle it.

“You just gotta ask: Can you take care of yourself?” advised John as he leaned against my camper, which he let me park on his Berkshires farmland. “If you can’t, you will always be looking for someone to take care of you. If you can, well, that takes care of the fear.”


His chickens clucked nearby and classical music poured out of his neighbor’s house. That’s the image I have of the Berkshires, Massachusetts’ rural hill-country enclave for the wealthy and local farmers too.  James Taylor lives here, as do many other celebrities and culture shapers. It’s a place with the finest local organic foods and pristine colonial homes on verdant hillsides owned by some of America’s wealthiest families. But it’s also home to rugged individualists and muddy-boot, blue-collar workers in farming and timber work. It’s perhaps the most liberal state in the country, but old-time locals fiercely defend their private property and right to bear arms.

John and Wendy, on their wonderful Brookmede Farm, kept me full with their farm-raised goat sausage and free-range eggs. Some of the most excellent food. Pure and clean. And I had the privilege of meeting their goats, pigs and chickens, all of whom John cared for by name. He fed them by hand three times a day.


I had many wonderful conversations with John and Wendy, on everything from their Berkshire pigs and Boer goats, to John’s work as an ad man in New York in the 60s, to the value of fending for yourself. John’s done just about everything. Film, advertising, business, construction, real estate, local politics and speechmaking, and farming. He’s dyslexic, and yet has been very successful in everything he does. Because, as I’m sure he’d say, he relies on himself and doesn’t expect anything from anybody. Although I’m sure Wendy being by his side for many years has something to do with it.


I had previously never met John or Wendy, and they opened their home to me and were so kind and generous. I had simply connected online with Wendy through my friend and fellow writer Greg, of, who I met at a dirt-road bus stop in a village in Costa Rica. So a bus-stop conversation led to me being hosted by a wonderful couple in their beautiful Berkshires meat farm. It really is amazing what can happen when we just open ourselves up to connection.


The Appalachian Trail meets the Berkshires just down the road from John and Wendy’s house. I took an hour or two and walked up the trail, in some of the most beautiful woods I’ve ever seen.


Through moss-covered birch and soggy lowlands leading around the bend, skirting farmland, to rocky, forested mountainsides. So peaceful. It was my first chance to hike in the past 2,500 miles, and it was so refreshing. I just had to take a self-portrait of me with the AT’s famous white blaze on a tree in the background, just to prove to myself I was really there.



The air is clean and quiet in the Berkshires. John let me fill up my freshwater tank with water from his spring-fed well, some of the sweetest water I’ve ever had. Clean and cold.

I pulled out slowly when I had to leave. It was so peaceful there. Then I drove down turnpike. John and Wendy’s farm is just up the road from Stockbridge, and the whole area is absolutely gorgeous. I listened to James Taylor’s “Sweet Baby James” as I drove down the “turnpike from Stockbridge to Boston….”

Two hours later, I was in Boston, hearing the Dropkick Murphy’s blaring out of a Towny’s Lincoln driving down Cambridge street. From Stockbridge to Boston is James Taylor to Dropkick Murphys. Big adjustment. Boston is loud and fast and, with Harvard, MIT, Berklee and other institutes of higher learning, one of the most intellectually stimulating cities in the world.


I stayed with my friend Chris, his wife Jen, and their dog Harley in a cozy apartment in Cambridge.


The first night I was there, Chris and I met his friends at a bar in Harvard Square. Chris and his friends are all highly educated, one of them being a nuclear physicist, and our conversation frequently turned into equations. Literally.


And so all in the same day, I woke up on a farm, had fresh-as-it-gets eggs and meat, filled up my tank with mountain spring water, and ended the day discussing the parabolic equation and string theory with physicists.


The next morning I awoke to horns, loud, engines, sirens, and some of the most articulate cussing I’ve ever heard coming from Boston tow truck drivers, with “B” tats on their necks, just outside my window. And then I had amazing Brazilian food that night to celebrate Chris’ birthday.

Berkshires to Boston. From spotless colonial summer homes and farmland to neck tattoos and Harvard Yard, this is all America. And so far as I’ve seen, all of it is beautiful.

One response to “Stockbridge to Boston

  1. Pingback: Sanctuaries of the In-Between: Thoughts from America’s Stonehenge and the A.T. | The ReStart Experiment·

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