11 Generations Later: Inside America’s Oldest Working Farm and Family-Owned Business in North America

After more than 400 years, Shirley Plantation remains both a working farm and a living record of American ag. Not only is it the oldest family-owned business in America, but it still unlocks pieces of America’s past.

Before America was a nation or the Declaration of Independence was even signed, this Virginia land was already being farmed along the James River. Today, that same ground continues to carry a family legacy that stretches back more than 400 years at Shirley Plantation. And as America celebrates 250 years of history, this family-owned business may be the key to taking a peak at hte past.

For Charles Carter, who owns Shirley today, he’s part of a strong history of family to live and work this land.

“I am the 11th generation of the family here on the land in this patch of land in Virginia. My son and daughter are the twelfth generation,” says Carter.

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Shirley Plantation, located on the James River in Virginia, is historically significant it is the oldest family-owned business in North America, with the Hill-Carter family continuously farming the land since 1638.
(Matt Mormann )

That legacy is proof history is not something preserved behind glass. Instead, it is still being lived. And if you walk inside the historic home, Carter points to a key that represents more than access. It represents continuity.

“It’s the longest continuous family-owned business in North America, according to the Institute for Family Enterprise,” he says.

America’s oldest family-owned business that’s also a farm. The Hill-Carter family has continuously farmed the Virginia land since 1638.

Farming Roots That Trace Back to Colonial Virginia

Shirley Plantation dates back to 1614, when early settlement farming first took hold along the James River. Tobacco was the original cash crop that helped sustain the colony.

“The land was granted in 1613, and there were people on the land farming by Christmas of 1615,” Carter explains. “The primary crop was tobacco, and that’s how the money was made for a long time here in Virginia. It’s what saved the colony.”

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From corn, soybeans and wheat, to the newest venture of pecans, the fertile farmland is still farmed today.
(Matt Mormann )

More than four centuries later, the operation has evolved, but farming remains the foundation. Corn, wheat, soybeans and even pecans now rotate through the fields, but Carter says the commitment to the land has never changed.

“I guess we’re stubborn,” Carter says with a smile."We like this spot and we have a family tradition I think that’s built up an identity. It’s good land, and it’s a beautiful place. It is worth fighting for.”

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A look inside the house that is nearly identical to what it looks like today.
(Cater Family )

More Than Land: Preserving Family History

For Carter, preserving Shirley Plantation is about more than maintaining historic buildings. It is about keeping generations of stories alive. A genealogy record tied to the family lists tens of thousands of descendants dating back centuries, including a direct connection to the early 1700s.

“The Carter genealogy book has 83,000 descendants listed from this man who died in 1732, the year George Washington was born,” says Carter while giving a tour of the house.

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The Carter genealogy book has 83,000 descendants listed from one man who died in 1732, the year George Washington was born.
(Carter Family)

Even the written records of past generations reveal how little some things have changed.

“It’s very interesting to be able to go read what your ancestors were saying, and you even get some snide comments and letters about people of the time. And it takes a little effort to get through some of the jargon, but it does provide a different window, a different way. Sometimes humorous,” says Carter. “I’ve seen people joking about plowing. They trash talk each other about their plows. Some things don’t change that much.”

A Schoolhouse Tied to American History

Beyond the main home sits a preserved two-room schoolhouse that once educated a young boy connected to one of the most recognizable figures in Civil War history. That student was Robert E. Lee.

“And in the early 1800s, there was a certain young man, a cousin, whose mother was a Carter from this house. He was sent here. And his father was Henry Lee, and his mother’s two favorite brothers were Robert and Edward. His name was Robert E. Lee. He went to school there. We’ve got it documented,” says Carter.

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Guests who tour Shirley have the chance to see a unique schoolhouse still standing, as it was where Robert E. Lee went to school.
(American Battlefield Trust)

Tourists can walk in the very schoolhouse that was used to educate Robert E. Lee. And many people have. At its peak in the early 1990s, Shirley Plantation welcomed more than 50,000 visitors a year. While tourism has shifted over time, Carter says the importance of connecting people to history remains as relevant as ever, especially as the nation approaches its 250th anniversary.

“I hope so. I hope that’s the way people see it, and not just as a passage of time,” he says. “As we talk about 250 years, 250 years is actually a very long time. And a lot of other countries had a significant change of style of government style of leadership, so getting 250 years under the same type of government, that’s almost impossible. And we’ve done it, and we need to keep doing it.”

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A two story schoolhouse still stands at Shirley, which is where Robert E Lee attended school.
(Matt Mormann )

Carter says it’s also an important lesson for the future.

“And we need grow. We need to to keep going. And the lessons of the past, I mean, you can’t drive forward looking backwards, but Lord, you could miss a lot of potholes if you know the pattern,” says Cater.

A Working Farm that Doubles as a Living Archive

After more than 400 years, Shirley Plantation remains both a working farm and a living record of American agriculture.

While many historic sites preserve the past behind museum walls, here, history is still planted, harvested and passed down from generation to generation. And it’s a piece of not just agriculture’s history, but American history, that’s still preserved today.

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Now stewarded by the 11th and 12th generations, the property has remained in the same family lineage, surviving major conflicts like Bacon’s Rebellion, the American Revolution, and the Civil War.
(Matt Mormann )

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