Charles Tompkins Matheson Sr., of The Plains, Virginia, passed away on October 8, 2026, at UVA Hospital in Haymarket, Virginia. He was born on August 10, 1941, the 4th child of “Pinky” Emma Henry(Tompkins) Matheson and Malcolm Matheson Jr. of Mount Vernon, Virginia.

Charles was a devoted father, grandfather, great-grandfather, brother, architect, artist, Christian, horseman, and sportsman whose life was deeply rooted in faith, family, creativity, nature, and traditions he cherished.

Charles married Bonnie Buchanan Matheson in 1961, and they had five children together. They began their married life while still teenagers, as he was attending the University of Virginia, working towards his degree in architecture. From Charlottesville, they moved to Kalorama Road in Washington, D.C., before moving to The Plains, Virginia, in 1970. Charles was also an entrepreneur. He owned the Black Walnut (cheese and specialty food store) with his younger brother John and The Liverpool Bit (a tobacco shop), as well as developed Mosby Square with his older brother Malcolm, all in Middleburg. As an architect, he designed residential and commercial buildings; schools and sports complexes, which he often incorporated the natural landscape into. He brought his creative eye and appreciation for proportion, design, and the surrounding landscape to his work. He knew how to make a mark on the land.

Charles’ architectural talents were also evident in his own home, Heathfield, where he and Bonnie raised their five children. For more than 40 years, he continually designed, built, added to, and improved the house, making it a reflection of his creativity and an enduring family home filled with memories.

Always surrounding himself with friends, Charley enjoyed his clubs. He belonged to the Chevy Chase Club, Metropolitan Club, F Street Club, National Tennis Club, Prince’s Court, Middleburg Tennis Club, Keswick Club, Knickerbocker Club, Spouting Rock Beach Association, and the Newport Reading Room, Orange County Hunt Club, where he served for many years on the board of stewards and was later president. He was a member of the Coaching Club in the United States and of the Coaching Club of Great Britain.

His education was important and decidedly Virginian, graduating from Episcopal High School in Alexandria, Virginia in 1959, then the University of Virginia’s Architecture School in 1964. His architectural talent was complemented by a lifelong passion for art. He was an accomplished painter, particularly known for his landscapes and allegorical works. Excellent works in oils, watercolors and pen & ink. Among his treasured artistic accomplishments was a book of his watercolors created while following the Orange County Hunt, called Hunting Sketches.

His love of the Virginia countryside naturally extended to horses and the traditions of the hunt. He was devoted to the sport of Fox Hunting, and he served as the president of the Orange County Hunt and served on their Board of Stewards for many years. Charles bred and raised Cleveland Bay and Thoroughbred/Cleveland crosses. He trained them for fox hunting and driving carriages and coaching. In the coaching world, he became an accomplished four-in-hand Whip. This sport took him on remarkable journeys throughout the East Coast and to England. As President of the Coaching Club, he traveled to London many times to drive in the great park at Windsor Castle and through the streets ofLondon. He also had the distinction of driving to the White House. He drove from Woodlawn to Mount Vernon, Virginia. He loved long-distance routes and driving from one historic destination to another. A favorite pastime was arranging a staged drive with several other coaching enthusiasts. Each driver drove their own horses on their stage, and when the horses were changed at the next staging point, the new driver took over with his own.

Like with the exclusive nature of driving road coaches, he also loved the game of kings, Court Tennis (Royal Tennis or Real Tennis), which he learned in Newport, RI during the summers he spent there at his wife Bonnie’s family home Beaulieu. He helped restore the ruined court at the Tennis Hall of Fame at the Casino in Newport. He was a co-lead in the efforts to build a new court in the Washington, D.C. Metropolitan area. He traveled to England and France to examine other courts for their dimensions and style before coming home to design Prince’s Court for the Washington International Tennis Club. Proudly considered one of the architects of the first court tennis court built in America in over 100 years. The glass sidewall he designed was unique at the time.

He loved to travel and teach. In Italy, he instructed watercolor painting to students in the Vicenza program founded by Mario Valmarana in 1975, as part of the University of Virginia for several years. He loved boats and later in life, bought a wooden Trumpy yacht. He named it Sirius. Fitted her out with his logo design of the Dog Star. Inspired by his grandfather, he loved the sea and irony.

For the last 45 years of his life, Charles devoted himself to helping others maintain sobriety and to have a spiritual awakening. He was deeply committed to serving others and valued those and the programs that supported him along the way. His willingness to share his experience, strength and hope with others was an important and meaningful part of his life and legacy. His encouragement and commitment paramount.

Charles’s life reflected his love of family, history, craftsmanship, horses, art, architecture, sports, Virginia and the land, and the people around him. He took great pleasure in preserving and participating in traditions while also leaving his own creative mark upon them.

Charles is survived by his wife, Julie Martin, and his first wife, Bonnie (Buchanan) Matheson; his five children and their spouses: Charles Tompkins Matheson Jr. and wife, Andrea; Helen (Matheson) Hilliard and husband David; Lilla (Matheson) Ohrstrom and husband Chris; Robert Redd Matheson; and John Murdoch Buchanan Matheson and wife, Susie; his 17 grandchildren and four great-grandchildren. Of his five siblings, Charles is survived by his sisters, Pinkie Matheson Roe and Sandy Roe, Torrey M. Cooke, and Lida Matheson Stifel and Rick Stifel. Including over 100 other cousins, nieces & nephews. Charles was preceded in death by his parents, “Pinky” Emma Henry Matheson and Malcolm Matheson Jr., and by his brothers and their wives, Malcolm Matheson III and Gail Matheson and William John Matheson and Petie Matheson.

Charles Matheson will be remembered for his remarkable creativity, his love of architecture and art, his devotion to horses, hounds and the traditions of the hunt, and his enduring connection to the Virginia countryside. His legacy lives on in his children, grandchildren, and great-grandchildren; in the homes and landscapes he shaped; in his paintings; in the traditions he loved; and in the lives of those he helped along the way.

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Charley and I were married for 43 years when our divorce took effect. Mostly very happy years, we grew our family and established ourselves in the Virginia countryside. We remained friends and kept in touch frequently because we had so many children and grandchildren, and ultimately 4 great-grandchildren to date. We had so many family events and holidays to share; it was lovely knowing he was around and paying attention. Now, that is over, and I am going to miss him.

Goodbye, Charley. I will never forget you.