The Highland Country Club was established in 1915. About 100 acres were purchased for $9750. Much of the land had been orchard. The southeast parcel consisted of pear trees. In the valley where hole number 2 was built, cherry trees grew and were enjoyed by the golfers until the 1960s. Along Blossom Lane were rows of Apple trees, with the last apple tree dying in 2006. William H. (Bill) Diddle designed the 9 hole course. The completed golf course opened on April 15, 1916. Alex Baxter was hired as the first golf instructor.
In 1931, club member E.O. Robinson planned to give the Club land on the north side of Blossom Lane for an additional 9 holes. Robinson owned large expanses of land and was in the lumber business. Several holes were laid out and irrigation pipes were installed. The day before the paperwork was to be signed and delivered to the Club, Robinson drove to Louisville on business. Usually his chauffer drove the car, but Robinson drove himself so that the chauffer could help his wife clean-up after a party that was held at his home the night before. On the return trip, Robinson's car left the road and he was killed. It is speculated that Robinson may have suffered a heart attack while driving. Because the paperwork was never signed, his heirs did not recognize the gift of the land to the Club. His estate offered the land to Highland for only $35,000. However at the height of the depression, the Club could not raise the funds. The course would remain 9 holes for another 50 years.
In 1983 the course planned to expand from 9 holes to 18. Land on the north side of Blossom Lane was finally purchased. By 1985 the new nine holes, laid out by Arthur Hills.
The clay and slate soil of the hills around Highland make the land susceptible to slippage. In an effort to correct several landslides and to improve the course, new tees were constructed for holes 12, 13 and 17 in 2000. Holes 12 and 16 were determined to be too close and number 12 green was moved 100 feet, allowing for a pond between the holes. Golf Course architect Jodi Kinney handled the rennovations..
Blue tees: par-70, 6,280 yards, 70.4 / 130
White tees: par-70, 5,818 yards, 68.2 / 126
Red tees: par-70, 4,799 yards, 68.4 / 120