Henry Montague Chiles, 90, passed away peacefully at his home in Batesville on July 18, 2026

A true force of nature, Henry was born in Charlottesville, Virginia, on November 20, 1935, to the late Henry and Virginia Montague Chiles. Raised in Crozet, he learned the value of hard work at an early age while farming alongside his father. After attending Hampden-Sydney College and serving in the U.S. Army, Henry returned home following his father's passing to lead the family orchard business with his aunt, the late Ellen Chiles Pickett.

In 1961, he married Ruth, and together they built a life centered on family, faith, fun, and agriculture. They continued the proud legacy of Crown Orchard Co., founded by his grandfathers, and Henry's vision and entrepreneurial spirit expanded the family enterprise with the creation of Carter Mountain Orchard and Chiles Peach Orchard. Through perseverance, long hours, innovation, unwavering determination, passion, and great enthusiasm, he transformed the family business into a lasting institution. His children and grandchildren proudly carry forward the heritage, values, and stewardship that Henry so passionately cultivated.

Henry was a pioneer in the apple and peach industry and was widely respected as a catalyst for new (and sometimes “crazy”) ideas. Known for his love of solving problems, belief in a handshake deal, and his ability to make friends and form lifelong relationships wherever he went, he brought that same spirit of enthusiasm and service to his industry and community. Over the years, he served on numerous boards, including the Virginia State Horticultural Society, the National Peach Council, USApple , the USApple Export Council, and the Central Virginia Electric Cooperative, where he was their longest serving board member at 46 years. As a lifelong member of Tabor Presbyterian Church, he served as a deacon, an elder, and past chair of the Building Committee.

Henry's dedication to agriculture earned him numerous awards and accolades over the years. Among those he valued most were being named Young Farmer of the Year by the Albemarle County Farm Bureau and receiving The Packer's prestigious Apple Man of the Year award in 2014

Henry is also remembered as a devoted UVA football and basketball fan. For more than 60 years, he rarely missed a game, traveling with family and friends to away matchups, ACC tournaments, and the 2019 NCAA Men’s Basketball Championship. Anyone who attended a UVA football game with him experienced his fun-loving spirit, bigger than life personality, and generous hospitality firsthand.

In addition to his parents, Henry was preceded in death by his wife of 60 years, Ruth Dollens Chiles, and his sister, Virginia Chiles Keith.

Henry is survived by his loving family: his children, Cynthia Chiles and her husband, Charlie Touchette, of Crozet; Huff Chiles and his wife, Judy Woodson Chiles, of Batesville; and Sarah Chiles of Crozet; his grandchildren, Lizzy Davis (Jordan), Ally Whitmer (Kevin), and Henry Chiles (Emily); and four beautiful great-granddaughters, Valerie Davis, Shelby Whitmer, Kinsley Whitmer, and Eliza Chiles.

He is further survived by his brothers-in-law, Thomas R. Keith of Ivy and Marvin W. Dollins (Dottie) of Waynesboro; sisters-in-law Charlotte Dollins and Eva Dollens, both of Crozet; nephews Randy Keith of Crozet and Henry Keith (Susan) of Ivy; numerous extended family members, and loyal employees of Crown Orchard Co.

Henry deeply valued his personal and professional friendships and leaves many close friends who cherish their memories of him. If you ever met Henry, you likely never forgot him.

Visitation will be held on Friday, July 24, 2026 from 4:00 p.m. to 7:00 p.m. at Tabor Presbyterian Church in Crozet.

Memorial services will be held on Saturday, July 25, 2026 at 1:00 p.m. at Tabor Presbyterian Church in Crozet, followed by a reception at the family home. Burial will be private.

Memorial contributions in Henry’s name may be made to the Tabor Presbyterian Church Building Fund, Crozet Volunteer Fire Department, North Garden Volunteer Fire Department, Western Albemarle Rescue Squad, and Hospice of the Piedmont.

Arrangements by Anderson Funeral Services, Crozet, VA