The city of Middlesboro, Kentucky, was established in the late 1880s by Scottish born Canadian Alexander Alan Arthur and his British backers in the American Association Ltd. They were drawn to the area by the promise of iron ore deposits in the Cumberland Mountains. Arthur purchased 80,000 acres of land and built his city in the Yellow Creek Valley of Kentucky.
The exact year in which the golf course opened is not definite, but 1889 is the earliest year that golfing has been confirmed. That makes the course the oldest continuously played course in the United States and the second oldest course in the nation. The course has had several names over the years. The original name was Kentucky Golf Club, later Middlesboro Golf Club, and the current name of the Country Club of Middlesboro.
In the early years there was no clubhouse. The 1st tee was located at what is now the corner of 25th Street and Worcester Avenue and headed west to Cirencester Avenue and then on to the remainder of the course that is still played today. In the 1920s the course moved west to accommodate the growing need for residential housing.
In 1889 30 men and women were members at the country club. Each paid the annual $2 membership fee. Of course, in the 1880s there were no golf carts. Golfers carried their own bags or used caddies. Some of the first caddies were Henry Sandifer, Ed Slusher, Mark Colgan, Paul Colgan, Arthur Rhorer, Ed Sampson, and Arden Kennedy.
By 1893 the boom in Middlesboro was over and the Baring Brothers Bank in London cancelled Arthur’s funding. The course continued to be used sparingly until 1921 when Judge Joe Bosworth Jr. helped reorganize the club and started on a plan of growth. The officers of the Club in 1921 were R.E. Howe – President, F.P. Scales – Vice-President, J. M. Milles – Secretary, and E.P. Nicholson – Treasurer.
In 1921 there were 150 members, and that was also the year the original clubhouse was constructed. In 1924 Middlesboro Country Club played host to the Kentucky State Amateur Championship.
For many years Middlesboro Country Club was also the home of one of the few Par 6 holes (660 yards) in the country. Number 7 was shortened to add flood control but remains a very challenging hole that few can reach in 2.