Hobart Cawood graduated from the Cincinnati College of Mortuary Science in 1928. He soon began working for Newman Funeral Home in Middlesboro, Kentucky. In 1932 he purchased the former residence of J.L Manring, a prominent Middlesboro business man, at 112 South 21st Street. After the purchase of the J.L. Manring home, Mr. Cawood started Cawood's Tri-State Funeral Home. The funeral home grew rapidly the first two years and Mr. Cawood soon found himself in need of assistance. He turned to his father, J. Frank “Pappy” Cawood, who soon joined the funeral home in the capacity of business manager. At this time the name of the funeral home was changed to Cawood Funeral Home. As the funeral home continued to grow Mr. Cawood was joined by his brother Pope Cawood who was a graduate of Gupton Jones College of Funeral Service. Pope was called away from the funeral home during WWII to serve his country in the Navy. Upon his discharge from the Navy he returned to the funeral home until his departure to co-found Perry & Pope Drug Stores in Middlesboro along with his dear friend Perry Siler.
Hobart continued to operate the funeral home along with his wife, Elnora, until their son Paul Connor Cawood, Sr., better known as Connor, joined the firm in 1963. In 1965, under the direction of Connor Cawood , the funeral home was completely renovated and remodeled, drastically changing the original structure, to accommodate the changing needs of the families being served. In 1964 Hobart went into semi-retirement turning day to day operations of the funeral home over to Connor and his wife Joan Asher Cawood. Connor continued to operate the funeral home until it was purchased by Clyde Creech and Jimmy Durham in January of 1978. Soon after, Mr. Creech purchased the interest of Mr. Durham. In 1986 Mr. Creech along with his wife Bonita Bingham Creech added a beautiful stone chapel to the north end of the original structure. This chapel is now used as the main chapel of the funeral home. It was built to allow the families the funeral home serves to experience the church atmosphere with convenience of being able to provide all services from the central location of the funeral home. Mr. and Mrs. Creech continued to operate and expand the funeral home until Mr. Creech's retirement in March of 2016.
After the retirement of Clyde Creech, Paul Connor Cawood, Jr., Hobart Cawood's grandson, joined the staff of Creech Funeral Home as business manager. The Staff is dedicated to the families the funeral home serves as well as the community and will continue to ensure the level of service the Cawood and Creech families and staff have provided since its founding.