A post office was established at Hollandsburg in 1853, and remained in operation until it was discontinued in 1902.[3] The community was named for a Kentucky minister named Holland who was a personal friend of John Collings, who built the first residence.[4]
Hollandsburg is the site of the 1977 St. Valentine's Day Massacre, in which four young men entered a trailer home and shot to death four brothers and wounded their mother.[5] Roger Drollinger, a 24 year old habitual criminal, expected to go to prison the next day on a drug charge, and decided to commit a thrill killing while he still had the opportunity.[5] Drollinger and his followers – Daniel Stonebraker, Michael Wright, and David Smith – were all found guilty of murder and sentenced to life in prison.[6] Roger Drollinger, then aged 60, died in prison on January 29, 2014.[6]