The South side of the Holly Springs Square is the oldest surviving section of the Square. Portions of the original 1830s Square can still be seen on both the southwest and southeast sides of the Square (look for the slanted roof lines). The South side of the Square was spared much of the destruction seen around the Square over the last 160 years, including Van Dorn’s Raid of 1862 which destroyed most of the east and north sides of the Square and the two major fires of the 1950s which resulted in the destruction of parts of the west and east sides of the Square. In fact, the first major fire to effect the south side of the Square occurred in 2016, when a fire destroyed the City Cafe building (but the rest of the south side of the Square was saved from damage or destruction).
Parts of the South Square can be seen in the earliest photograph of Holly Springs, a 1857 ferrotype now owned by the Dancy family. The entire south Square can also be seen in the Alexander Simplot drawing of the Square from 1862 (see pictures above).
At the southwest corner of the Square is the Utley Building, which has housed many businesses over the past 175 years but is most well known for being the location of several drugstores, the first of which was owned by J. H. Athey. Athey’s drugstore was the only business in town that survived both the Civil War and the Yellow Fever Epidemic relatively unscathed. In 1887, the drugstore was bought by Lytle A. Rather (1859-1930) who ran the store for several decades. In the early to mid 20th century the drugstore was owned by Lucius H. Dancy (1884-1940).
To the east is the Shepard Smith Cotton Company Building, once owned by the father of Fox News reporter Shepard Smith. Before the cotton office, this building was used as several kinds of merchant stores, including a bowling alley. The second floor of this building contains a beautiful bay window added in the early 20th century. Continuing east is one of two surviving buildings from the original 1830s Square. In the early 20th century it was home to McDermott’s Cafe, but is most famous as the Cecil Cottrell (1896-1985) Grocery Store. The last two buildings on the southwest side of the Square are today home to JB’s Restaurant. In the late 1800s and early 1900s this was the home of the Shumaker Brothers clothing store, owned by the Jewish Shumaker family. The original Shumaker Bros tile floor at the main door can still be seen today. In the mid 20th century this was home to the Hamilton Harris Dry Goods Store, until Harris was murdered is his Store in the 1950s.
Crossing Center Street, the next building going east is today the home of the Byers Law Firm, but was known as the Rather Drug Store for many years. In the middle of this block is another remnant from the the 1830s Square (this exact building can be seen on the 1857 ferrotype posted above). At the end of the South Square is a building which was largely destroyed in a fire in 2016. In the late 19th century it was used as a dry goods store. For much of the early 20th century it was known as the Lucas Furniture Store, with a morgue located in the back. This furniture store/morgue turned into the City Cafe by the 1930s, and lasted for seventy years. JB’s Restaurant was the last business to use the building before the fire.