Holly Grove, the third largest community in Monroe County, was incorporated in July 1876. John M. Smith and James Kerr were two of the earliest pioneers, both arriving when the site was but a group of Holly thickets from which the name of the town was derived. The name was chosen in 1872 by Mr. and Mrs. J. M. Smith and Dr. A. K. Roberts.

In 1871 Monroe County subscribed $100,000. for the building of the Arkansas Central Railway, later known as the Arkansas Midland Railway. The tracks were completed and in 1872, a depot was erected and the town of Holly Grove became an important station on the route between Helena and Clarendon.