The first stores and buildings on the North side of the Holly Springs Square were built in the late 1830s, soon after the construction of the first frame Courthouse. These early buildings would have been made mostly of wood. Not much is known about the northwest corner of the Square until 1858, when the City of Holly Springs gave the firm Bradley and Company a ten year exclusive liquor license in town, in exchange for the construction of the Magnolia Hotel, a grand three-story brick structure with ornamental iron grill-work. This Hotel would have been one of the largest hotels in Mississippi at the time it was built.
On the northeast corner of the Square was located the Williamson Hotel (also called the Marshall Inn), which was another hotel and where the local stage coach office was located. All other records of shops and stores on the North Square were wiped out on December 20th, 1862, when Confederate Earl Van Dorn’s Raid against Union-occupied Holly Springs resulted in the destruction of the entire north side of the Square, including the short-lived Magnolia Hotel.
Between 1872 and 1875, much of the North Square was rebuilt, this time in brick and stone, in the Italianate and Renaissance Revival styles of commercial architecture, including window arches, stamped-metal window cornices and decorative roof parapets. The northwest corner of the Square was anchored by two imposing buildings: the Italianate building on the west side which housed a Confectionery Store in the 1880s (but is more well known as the site of the First State Bank in the 20th century) and the Renaissance Revival building on the east, which held a Jewelry Store for much of the late 19th century and early 20th century. During the middle of the 20th century the St. Louis Bargain Store, run by Stanley Barnett, was located in this building. The building to the east of the First State Bank building was the town’s main Barber Shop for much of this period (see 1886, 1902 and 1915 Sanborn maps). On this same block was empty land until the 1930s, when a Art Deco building housing the Holly Theatre was built (see 1933 Sanborn Map). The Holly Theatre would be one of the major recreational centers of the community for 40 years, before closing in the 1970s. This section of the North Square would later be home to the Burch Realty Office, Robinson Drug Store and Stubbs Department Store.
The northeast corner of the North Square has retained its’ architectural cohesion better than the northwest corner. Much of this section of the Square is Renaissance Revival, with a central section of semicircular arch windows and stamped-metal cornices and prominent dentiled roof cornice. The western portion of this section had stores which changed ownership frequently, with Grocery stores, Dry Good stores and even a second-story photography studio represented in the historic record. Sam Coopwood, future Mayor of Holly Springs, had a dry goods store on this section of the Square in the 1930s and 1940s. Today, the Southern Eatery restaurant is located in the same space. Next door was once the Pure Drug Pharmacy, where one of the most notorious murders in Holly Springs history (of storekeeper Marcus Louis in the 1870s) took place. On the northeast corner of this section was Norfleet and Sailor, a Furniture and Funeral Parlor (a very strange combination today, but quite standard in the 19th century) which stood here for several decades. Later the building was home to the Sigman Brothers Grocery Store in the early 20th century, and then later would be home to the Armor, and finally Seale Drug Stores. Today the Court Square Inn is located in the same building.
The small alleyway between College Avenue and Falconer Avenue was known for many years as “Hell’s Half Acre”, due to the criminal activity which would often occur in this area. Throughout the first half of the 20th century, the North Side of the Square was closed off to traffic during elections for the popular election night result parties which would be held here.