Chatmoss Country Club 's roots date back to the late 1780's where today's clubhouse was part of the Hairston Plantation. The first two-story cottage was built as a wedding gift to Alice Hairston when she married Sam Harden around 1800. The property then became known as the Harden-Hairston Plantation. Shortly after adding a third story to the building, a fire destroyed the home and most of the outbuildings.

In 1928, an Old English style brick plantation 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. Remnants of these boxwoods, not quite in their previous glory, can be seen on the 10th tee. 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.