The Chiles family has been in Albemarle County for over 100 years, with several generations of farmers named Henry working the land. For anyone familiar with the family, though, one Henry Chiles will always stand out. As an orchardist, a businessman, a leader, a husband, a father, and much more, Henry Chiles (1935–2026) left an unforgettable legacy. We said goodbye to him in July 2026. He was 90 years old.
Henry Montague Chiles was born in Charlottesville, Virginia, in 1935. His grandfathers had founded Crown Orchard Co. only 23 years prior, and Henry grew up in the orchards, learning the trade firsthand, from growing and picking to packing and shipping. Though he left to attend Hampden-Sydney College and serve in the U.S. Army, Henry returned home to lead the family business after the passing of his father.
Henry’s intuitive sense for the fruit business, backed by hard work, perseverance, and passion, quickly helped Crown Orchard become one of the most successful orchards in Virginia. Among apple and peach growers, Henry Chiles had a reputation as an innovator with some “crazy ideas,” but also a wealth of integrity and a community spirit that built lifelong relationships and brought domestic and international recognition to the Virginia fruit industry. With Henry, you knew a handshake deal would be honored, and any problem would be solved with unwavering optimism.
Henry, Ruth, and the Growth of Pick-Your-Own Fruit
The defining partnership of Henry’s life, both in love and in work, was with his wife Ruth Dollens Chiles, whom he married in 1961. They relied on each other at the orchards, including during the tricky freeze of 1974. Without enough fruit for a full season of hired pickers, Henry and Ruth instead thought to take out an ad in the local paper inviting people to come out and pick their own peaches. From a simple roadside stand with a card table and a set of scales, Ruth saw the community pour in. It turns out lots of folks were eager to experience the pure joy and natural connection of picking fruit fresh from the orchard!
It was clear that the public shared a little of their peach passion. That card table was the start of the Chiles Peach Orchard we know and love today. Now, the orchard offers pick-your-own apples, peaches, flowers, pumpkins, berries, and more from spring through fall. Henry was a reliable and insightful leader as the family business expanded into agricultural experiences for the public, including beloved Charlottesville institution Carter Mountain Orchard, the sweet cherry-growing Spring Valley Orchard, and most recently in 2021, Chiswell Farm & Winery. Ruth passed away in 2021. She and Henry had been married for 60 years.
A Proud Virginia Legacy
Henry Chiles loved his home, community, and the agriculture industry here in Central Virginia. He was a leader in organizations such as the Virginia State Horticultural Society, the National Peach Council, USApple, and the U.S. Apple Export Council. At 46 years, he held the record as the longest-serving board member of the Central Virginia Electric Cooperative.
The industry honored him numerous times throughout his career, including as the “Young Farmer of the Year” by the Albemarle County Farm Bureau, and as “Apple Man of the Year” by industry publication The Packer in 2014. Crown Orchard was named a Virginia Century Farm in 2012, commemorating its 100-year history. For over half of that century, Henry was in charge.
In his personal life, Henry Chiles was a lifelong member and volunteer at his church. If he had a passion outside of apples or peaches, it was for UVA sports. He was an unwavering supporter of his hometown team through good seasons and rough ones. Across six decades, he attended as many UVA football and basketball games as he could. You would find him at home games, away matchups, ACC tournaments, and championship matches. Henry loved bringing family and friends together to experience the joys of his life, whether it was at home, among the trees, with his employees, or in a stadium with thousands of other fans.
Henry Chiles was in the third generation of farmers to care for the family’s orchards. Today, the torch has been passed to the fourth and fifth generations, his children and grandchildren. Together, they manage every aspect of the business guided by the lessons and examples Henry set before them. The sixth generation, his great-grandchildren, spend plenty of time in the fields and orchards, growing up surrounded by fruit trees just like Henry did.
