From New York to Wisconsin

REEDSBURG, Wis. — Robert Van Valkenburgh made his living milking 30 Holstein cows at an upstate New York dairy farm. He did not realize that his life would create a legacy that would extend beyond New York and find a home with his great-grandson, AJ Wilson, in Wisconsin’s Driftless region.

“My great-grandfather was always working on the farm,” Wilson said. “My mom’s side of the family came from that. He’s been a dairy farmer, milking at the same place for 75 years. He was part of the inspiration for me to own my own farm.”

On Sept. 9, Wilson’s dream became a reality as he milked his herd of 15 registered Guernseys and Jerseys  in a rented barn outside of Reedsburg.  He plans to grow the herd, purchasing two head that are immediately ready for the milking barn and six that will freshen in 2025. Wilson plans to raise the calves on the property that houses his milking herd.

The move to Wisconsin was a leap of faith for the farmer from New York, but a career in agriculture was something Wilson had always worked towards. He began his journey to dairy ownership near Carlisle, New York. As someone who did not grow up on a farm, his great-grandfather’s farm near Summit was where his love for agriculture was born. Spending time there throughout his childhood started the agricultural fire within him.

At 16 years old, Wilson worked for Clayhill Farms in Central Bridge, New York, for Jacob and Howard Cornwell. There, he helped make 800 acres of hay on the beef and crop farm. 

“I decided that sort of agriculture wasn’t for me,” Wilson said. “I wanted to milk cows.”

He then found a position with a 300-cow Holstein farm in New York called CDS Tillpaugh. He milked cows in a double-8 herringbone parlor, working for Stewart and Meghan Tillpaugh and Derek Herringshaw.

After that experience, Wilson decided to try something a little less conventional, and at 20 years old, moved to Bozeman, Montana, for a chance to milk cows in a different part of the country.

“When I moved to Montana, I just went farm to farm looking to see if anyone needed help,” Wilson said. “I ended up working at a 230-cow dairy where they were milking in a double-8 herringbone parlor too.”

With more experience under his belt, Wilson decided to move back to his home state of New York. On the over 2,200-mile drive back to the Empire State, Wilson stopped in Dodgeville, Wisconsin and knew the dairy state was where he wanted to end up.

“I knew I wanted my own place, and this area reminded me of home,” Wilson said. “This area, to me, is the last remaining place in the country that I feel somebody can start milking cows and be successful. There are more markets, and I just thought this was the place I wanted to be.”

A few years later, Wilson returned to Reedsburg, working at a job in town before being introduced to Janice Hill, who milks a 40-cow herd of Brown Swiss crosses in a tiestall barn. Wilson worked with Hill for 3.5 years with a goal to find his own space while he built up his herd.

Wilson found potential just a minute away from Hill’s farm. A challenge was that no cows had been milked in the barn since 1994 and there was no pipeline. He asked the owner, Kevin Labansky, if he could renovate the barn to make it suitable for milking, and Labanksy obliged. Wilson set about getting stainless steel, a bulk tank and the other essentials for pipeline milking in 2025. Jim Young helped do the work to bring Wilson’s dairy dream to life.

The 16-month project finished up in early September, and soon after, Wilson moved his herd from Hill’s dairy to his own. He was living his dream, milking cows in a tiestall barn, spending his days taking care of the animals that would take care of him.

The second day of milking is when everything sank in. Everything he had been working for was a reality. All the doubts that he faced and challenges he overcame seemed to wash away.

“I milked cows for other people for 10 years, and now finally I get to do it for myself,” Wilson said. “I worked in town, worked odd jobs, it all led me to here. Now I get to milk cows. I’m free.”

The responsibility of it all also hit him that second day.

“The other thing I realized was that it’s all on me,” Wilson said. “I was responsible for cows before, but now their well-being is 100% on me. It’s one thing to overcome the challenges to get to this point. It’s another to make sure I find a way to never lose it. Janice and I talked about the pressure that comes with that. The stress on day one is the same she feels in year 19. I’m ready for that, and I’m ready for this challenge.”