Virginia is for Olivers: 20 Year Collection

A Virginia man collects and works Oliver tractors like those he grew up with, including a Row Crop 77 that took over 20 years to acquire.

By Rocky Womack
Updated on July 8, 2022
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Photo by Rocky Womack
Robert Gregory’s Oliver 1755.

Robert Gregory’s youth in Pittsylvania County, Virginia, was spent on Oliver tractors. He remembers adapting a 1965 Oliver 1550 by front-mounting a John Deere 2-row cultivator onto the frame.

“It was a tricycle tractor,” he says, “and you’re sitting way up. It was perfect for plowing tobacco. Two rows were the thing back then, not four.”

Later, farming in Java, Virginia, Robert used the modified Oliver to cultivate flue-cured tobacco at night, when the leaves were more upright, allowing him to push soil closer to the plant.

One morning at about 3 a.m., he was cultivating when he became drowsy. “I was just going to put it in neutral when I got to the end of the field, and I’d lay my head on the steering wheel and leave the tractor running for like two minutes,” he says. “The next thing I know, the sun is up. I’m still sitting there, and that tractor’s running. I was asleep with my arms and head on the steering wheel. I will never forget that. I put most of my teenage life in on that thing. I mean, long days!”

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