Chatmoss Country Club's roots date back to the late 1780s. Today's clubhouse was part of the land owned by the Hairston family. The first two-story cottage was built as a wedding gift to Alice Hairston when she married Sam Harden around 1800. Soon after, a third story was added to the building. The Hairston family remained in ownership throughout the 19th century. In the early 20th century a fire destroyed the home and most of the outbuildings.

In 1928, an Old English-style brick home was rebuilt on the site which was later incorporated into the present clubhouse. The owner, Ruth Hairston Simms Schaeffer was the last resident and adopted the name Chatmoss from an English novel that she was reading at the time. Mrs. Schaeffer and her second husband shared a love of gardening and the outdoors. She claimed to have the largest boxwoods in the world boasting over 40 feet in height. The Boxwood Grille carries the name of Mrs. Schaeffer's passion.

Ready to leave the area, Mrs. Shaeffer offered the land to Mr. Fred Renick for $125,000 in 1955 who joined forces with several other Martinsville businessmen to officially form the Chatmoss corporation.