Herding Cattle and Tourists to the Montauk Plain

I find it amazing how little we really know, or in many cases, even care, about our ancestors. In many other cultures, like that of our Shinnecock neighbors, ancestry is sacred and details are passed from generation to generation.

The East End’s very own Gwyneth Paltrow is partly to blame for my recent fascination with this issue. In 2011, she was featured on the television show Who Do You Think You Are? On the show each week, a different celebrity goes on a journey to trace his or her family tree. That was the catalyst for me to explore my own family history. It took a couple years, but I finally got the information I sought.

To my surprise, I discovered that my great grandfather and his father were both horsemen who, on occasion, sought to earn a wage by driving cattle up the trail. That might explain why I’m a fan of the old western movies. Unfortunately, information as to exactly what specific cattle trail they drove was not available.

I recently read that East Hampton’s Main Street was where, for more than a century, the annual cattle drives to Montauk began. This was, of course, before the Hamptons became so commercialized.

The cattle from East Hampton and the surrounding areas were driven to Montauk in the spring to pasture and then returned via the same route in the fall. This got me fanaticizing about the feel of leather on my backside and the sounds and smells of bringing the herd to summer pasture. The sun would be shining on my shoulders as I kept the herd in check. Yes—being part of a good old-fashioned cattle drive was what I longed for.

That gave me an idea wherein I could pay tribute to those who came before me and perhaps create a sense of nostalgia for others at the same time. It was really pretty simple—I would rent some cows and run them up through Main Street just before summer. I had no idea what I would do when I got to Montauk, but I figured every adventure has its challenges and unknowns.

This was important to me and I vowed that I would not be deterred. I was pretty certain there were many horsemen and horsewomen in the Hamptons who would be willing to help me drive them little doggies. Matt Lauer, Christie Brinkley, Richard Gere and others are known horse aficionados. Maybe I could even get Gwyneth to ride along.

However, my excitement was soon dimmed. History be damned as I ran into roadblocks every step of the way. Permits, town meetings, insurance, emergency services personnel, poop clean-up, etc.

“What about the cows?” I asked. “They need that Montauk grass”

“Sorry” was all I got.

It was as if the past was being ignored, in favor of the new and improved East End. All I wanted to do was to bring a little bit of history back to the people and at the same time make my ancestors proud. I had a good mind to just run the herd anyway and let the chips, both cow and otherwise, fall where they may.

Then a thought came to me.

What if, instead of cows, I could just herd a bunch of tourists up the road a bit?

It would be sort of like herding cows. Most of these people would undoubtedly be wearing or carrying leather, whether it be shoes, skirts, belts, wallets or purses.

Sure they would try to get away, but I expected a certain number of cows would have attempted the same. And besides, tourists aren’t really that much smarter than cows.

I don’t believe there are any laws on the East Hampton books that specifically prohibit “tourist herding.”

In some way, this might even be better than herding cows, because those tourists who make it to Montauk will be thirsty and in need of refreshments. That might bode well for the merchants. Perhaps this will become an annual event like the Running of the Bulls in Pamplona. Locals might even start referring to me as a cowboy hero.

Yes—we should honor our history, personal and otherwise.

Now I just need to find someone who will lend me a horse, saddle and possibly bail money.