The West Holly Springs Square consists of a central section of mid-19th century buildings in between two much later additions.  Not much is known about the buildings and stores located on the West Square before the Civil War.  It is thought that the Union Army Hospital was located on this part of the Square during Van Dorn’s Raid.  The northwest corner in the late 19th century was originally office space, a drug store and stables (see 1887 Sanborn Map).  At some point between 1887 and 1892, the entire northern half of this section of the Square was completely destroyed (likely by a fire), leaving an empty lot (see 1892 Sanborn Map).

In 1904, the Odd Fellows Building was built on the north part of this section.  In the early 20th century, the Odd Fellows club used the second floor of the building as their meeting hall, while the bottom floor housed Clark and Tyler Whosesale Grocers.  Later, a movie theater was located in this building, and for much of the late 20th century an auto parts store was located here.  As of 2017, an antique store is located in this building.

Next door is a mostly-empty lot, which was never completely rebuilt after the 1890s fire.  A small cottage was built in the back of the lot in the 1940s, and the cast iron fence that surrounds this lot used to be located around the Courthouse across the street.

The Bank of Holly Springs is one of the oldest continually-operated banks not just in Holly Springs, but in the entire State of Mississippi.  It has been located in this same building since it was founded in 1869.  In the 1910s a limestone veneer was placed over the brick edifice of the Bank in the Beaux Arts classic style.  The next building south has now been incorporated into the Bank of Holly Springs, with a limestone veneer as well, but this was a separate store for many years.  For part of the 20th century this was a grocery store run by the Athey family.

The next three buildings south of the Bank of Holly Springs were built in the Renaissance Revival style in the 1870s building spree.  All three buildings have pedimented or dentiled roof cornices and iron metal window lintels.  These stores consisted of a Confectionary store, a hardware store and later was home to the Anderson and McCrosky Feed Store.  In 2017 an insurance company has offices in these buildings.

The southern-most corner of the West Square was altered beyond recognition in the 1950s after a devastating fire destroyed the two buildings at this corner.  The north building was known as the Groskins Mercantile Store for the early 20th century before it was incorporated into the next-door Stafford’s Cafe.  This building was a local landmark for many decades in the late 19th century until the middle of the 20th century.  During much of the 20th century it was run by William Gordon Stafford (1889-1965).  Below Stafford’s Cafe was the local bus stop, and the Cafe likely saw much traffic from the bus stop.  Stafford’s Cafe was also known as a local “hang-out”, and many children had their birthday parties and celebrated other special occasions in one of the Cafe’s special rooms.  Senator Wall Doxey has his law offices above Stafford’s Cafe.  On December 13, 1956 a fire destroyed Stafford’s Cafe, the Doxey law office and the Landreth Sporting Goods Store next door.  This irreplaceable building was destroyed and a modern building was built on its spot.

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