Since Chiles Family Orchards’ humble beginnings, five generations have had a hand in building a beloved agribusiness and some of the area’s favorite traditions.

These days, it takes lots of people to keep our farms running–and most days, you will see members of the Chiles family, as well as our amazing staff, here to greet you, teach you about the fruits we grow, serve you a cider donut, and thank you for visiting our family farms.


Cynthia Chiles holding crate of peaches

The planting of the original orchards and the start of a legacy.

In the early 1900s, Henry Chiles and John Montague planted peach trees for commercial production. From this small farm in the Crozet area, peaches were packed and shipped all over the country.

Thus sparked the founding of Crown Orchard Company: our wholesale business as Central Virginia fruit growers, packers, shippers, and exporters. We supply orchard-grown fruit to grocery chains and military commissaries up and down the East Coast. We even export apples internationally!

(Pictured: Cynthia Chiles, Fourth Generation Farmer)

Early 1970s

View of the sun shining over Carter Mountain fields

The Chiles Family begins harvesting on Carter Mountain.

The land on which Carter Mountain Orchard sits is rich in Virginia history! The unique mountaintop location changed hands several times in the past 200 years. We began operating Carter Mountain Orchard as a commercial apple orchard in the early 1970s and officially purchased the land in 1985.

History Lesson

According to research done at the Albemarle County Historical Society, the Honorable John Carter, Esquire (pictured) obtained by grant 9,350 acres of land which embraced the whole of what is still called Carters Mountain, in 1729.

Carter was at one point the Secretary of the Colony of Virginia. Upon his death in 1742, his land was given to his son Edward. Edward represented Albemarle County in the House of Burgesses from 1767 to 1769, and in the House of Delegates from 1788 to 1792.

In 1771, in exchange for legal services for Edward Carter, Thomas Jefferson received “as much of his (Carter’s) mountain as can be seen from mine, and 100 yards beyond the lines of sight agreed before Captain Burton” (documented in the papers of Thomas Jefferson). This land is owned by Monticello and is adjacent to Carter Mountain Orchard.


Huff and Henry Chiles examining peaches in the orchard

The start of “Pick Your Own” after an almost total freeze-out.

As peach season approached, there was not enough fruit to bring in seasonal pickers or run our packing house. So, we decided to open up the orchard to the public and let them pick what few peaches we had. 

It began with a card table, cigar box, set of scales, and a roadside stand. We placed an ad in the local newspaper and wondered if anyone would come–remember, this idea of “Pick Your Own” was a fairly new concept at the time. Fortunately for us, the public did indeed come! We sold all the fruit we had that year and called it a success. 

We originally intended for this to be a “one-shot” deal to get us through a rough year. Imagine our surprise when the phones began ringing the following year, wondering when we were opening for “Pick Your Own”!

(Pictured: Huff & Henry Chiles, Fourth & Fifth Generation Farmers)

Read “Meet the Growers of Chiles Peach Orchard and Farm Market” by Wine & Country Life


Ruth Chiles and family at country store

“Pick Your Own” is here to stay!

Since the public had been so good to us the previous year, we felt we could not say “no”. So, we set aside a few acres of peaches for “Pick Your Own”, built a tiny temporary shelter, and put up a sign. Ruth Chiles and one other employee worked seven days a week to sell the peaches and apples. It was a hit! 

We soon added berries, sweet cherries, pumpkins, vegetables, and flowers to our “Pick Your Own” crops. Plus, wine grapes were added to the wholesale offerings. Long story short, the public was getting a hunger for fresh fruit straight from the farm.


Ruth Chiles leading Come Grow With Us

Carter Mountain Orchard begins hosting school field trips. 

In the 1980s, Carter Mountain started offering educational school field trips to share the harvesting experience with Albemarle County’s next generation of farmers. 

Now, both Carter Mountain Orchard and Chiles Peach Orchard offer field trips to pre-schools, elementary schools, summer camps, and homeschool groups. We love providing an enjoyable and educational environment for children!

(Pictured: Ruth Chiles, Third Generation Farmer)


Carter Mountain Orchard farm market

Peach trees planted at Carter Mountain Orchard.

To extend the season at Carter Mountain, we planted some peach trees, which allowed us to offer delicious fruit to pick in both summer and fall. 

The addition of the bakery in 1995 was an instant success. In fact, our fresh apple cider donuts are still one of our best “attractions”!

As the years passed, we slowly took over more and more of the Apple Barn, making room for our Country Store. We built restroom facilities, made a LOT of parking space, and entered the world of cash registers, credit cards, and internet marketing! As the demand for apples quickly outpaced our supply, we set aside more apple trees for pick-your-own.


Chiles Peach Orchard Farm Market and Bakery

The Chiles Peach Orchard roadside stand gets a big upgrade. 

Over the years, we enlarged our roadside stand (twice!) to accommodate the influx of orchard lovers. We even knocked down a few trees to make space for parking spots, but that still didn’t meet the demand of the new millennium. Right before our eyes, that small roadside stand transformed into a beautiful new Farm Market. We quickly stocked the market with jams, jellies, crafts, and gifts to complement our fresh fruit.


Pick your own cherries in Virginia

Spring Valley Orchard opens to the public.

While the cherry orchard belonged to the Chiles family for years, we first opened its doors to the public for pick-your-own sweet cherries in the summer of 2008. 


Chiles Family

Celebrating 100 years of farming in Albemarle County, VA.

We were honored to become a Virginia Century Farm (as “Crown Orchard Company”). The Virginia Century Farm Program recognizes and honors those farms that have been in operation for at least 100 consecutive years, as well as the generations of Virginia farm families whose diligent and dedicated efforts have maintained these farms, provided nourishment to their fellow citizens, and contributed so greatly to the economy of the Commonwealth.


Chiles Family Orchards goes solar.

Our family understands that everything we do is dependent on Mother Nature. So, it’s only natural that we give back where we can. Our solar array includes 559 solar panels on Carter Mountain, 224 at Chiles Peach Orchard, and 2,040 at our Covesville production facility.

Also included in these exciting additions was the construction of our pavilion and courtyard space at Chiles Peach Orchard.


Carter Mountain wine bottles with a scenic view

The year of wine!

Our family has been growing and harvesting grapes for area winemakers for decades. After an abundant grape harvest in 2019, we decided to use surplus grapes to launch our very own wine label! Now, those grapes comprise our first vintage—a Petit Manseng—which was released to the public in May at Carter Mountain Orchard’s Thursday Evening Sunset Series.

We opened the Wine Shops at Carter Mountain Orchard and Chiles Peach Orchard during the summer and began welcoming visitors to Chiswell Farm & Winery in the fall.