Cynthia Chiles carries a box of Carter Mountain Orchard peaches at her farm store.

Since 1912, the Chiles Family has been farming in Albemarle County, Virginia.

Beginning with a card table, cigar box and roadside stand, the first generation of the Chiles family farmers sold the fruit of their labors to neighbors and folks passing through.

“The farm was started by my two great-grandfathers,” said Cynthia Chiles, one of the fourth generation farmers and owners. “Originally we were a commercial wholesale peach and apple operation, focusing on growing, packing and shipping. Then we ended up diversifying into direct marketing in the ’70s, and we added small fruits and berries, pumpkins, sweet cherries, flowers and vegetables to our pick-your-own and direct marketing. We also began growing wine grapes and wholesaling them to other Virginia wineries in the area.”

Gradually over the next 45 years, the farm continued to expand. Starting from the pick-your-own stand in the 1970s, then the farm bakery and school field trips were added in the 1980s, and the farm began hosting private events in the 1990s.


Vegetables are sold at one of the Chiles' retail locations.

“We kept listening to customers, trying to anticipate and stay ahead of the trends,” Chiles said. “We took a lot of risk, but we’ve made it all work by incorporating our growing family into the businesses, as well as key managers and staff who have been with us for a long time. The third, fourth, and fifth generations of family are still working on the farm, planting and pruning, managing the markets, overseeing harvests, running the agritourism businesses, and providing fresh produce to central Virginia and beyond.”

The family farm business has grown so much it now operates from five locations in Virginia: Chiles Peach Orchard in Crozet, Chiswell Farm & Winery in Greenwood, Carter Mountain Orchard in Charlottesville, Spring Valley Orchard in Afton and the Ivy Road Pop-Up stand, also in Charlottesville.

The business leveled up again in 2019 when they went solar. Tucked near the tree line of Carter Mountain Orchard, on the rooftop of Chiles Peach Orchard’s Farm Market, and at the production facility in Covesville, are vast solar arrays providing power for orchard operations. The orchards have a combined 2,823 solar panels.

A Family Tradition

When asked how the family is able to manage an operation of such size, Chiles said, “It takes an entire team.”

Chiles’ father, Henry, at 85, still manages the wholesale operation, the packing house and export sales. Chiles herself manages the pick-your-own operation as well as the retail and hospitality division, which includes both retail wine locations. Her brother Huff manages the 1,700-acre farm production and farm infrastructure, and his wife, Judy, is the business manager. Chiles’ sister Sarah manages food safety and quality assurance.

The fifth generation of the family is now in the business as well, helping with retail, production and marketing.


Huff Chiles holds a peach in his family's orchard.

“Of course, we couldn’t do it without our fabulous farm staff either,” Chiles said. “From the guys in the fields, to the managers and retail staff, everyone we hire is important in the running of the business.”

All the products, amenities and entertainment they offer, combined with passion and dedication to a quality customer experience, it is no wonder that the family farm locations have become community favorites and a destination for visitors far and wide.


The Chiles family have over 2,000 solar panels at their various farm locations.

The orchards and wineries attract a lot of tourists, but also have a loyal following of local customers.

“It’s a nice mix of both, but the locals know to stay away on the weekends to avoid the tourist crowds,” Chiles said.

With so many operations and customers, Chiles said they have been dealing with a shortage of labor.

“Many customers simply don’t believe we can’t find enough help and have shown impatience and frustration,” she said. “We deal with it as with any other challenge of any other year — with our best smiles and thick skin, our hospitality and sometimes bitten tongues, our camaraderie as a family and a team, and with the knowledge that everything is a cycle. And what helps more than anything, is that we love what we do.”


What To Read Next