At one time or another, many (and maybe most) early twentieth-century households in East Wilson had one or two lodgers or boarders, but few dwellings actually operated specifically as boarding houses. In the 1916 version of Hill’s Wilson, N.C., city directory, the only Black-owned boarding house is listed is that of Olivia Simmons, way down South Lodge Street at its crossing with the Norfolk & Southern railroad.

A broader look at Simmons’ addresses suggests the boarding house was, in fact, not on South Lodge, but on the narrow road running alongside the railroad.

In the 1908 Hill’s Wilson, N.C., city directory: Simmons Olivia h N & S Ry bet Factory and Lodge. In 1908, Simmons’ house would have been on a nameless dirt track fronting the railroad and running between Lodge (to the northwest) and Factory (parallel to the Atlantic Coast Line railroad to the southeast).

In May 1910, the Wilson Daily Times published Olivia Simmons’ name in a list of delinquent property tax payers.

In the 1912 Hill’s Wilson, N.C., city directory: Simmons Oliva cook h N S R R nr Lodge

In the 1916 Hill’s Wilson, N.C., city directory: Simmons Olivia (c) boarding S Lodge and h N S R R tracks

In the 1920 Hill’s Wilson, N.C., city directory: Simmons Olivia cook h N S R R nr S Lodge

In the 1920 census of Wilson, Wilson County: on Lodge Street, Olivia Simmons, 51, widow; daughter Rosa, 23; and granddaughters Lula, 14, and Reda Knight, 8.

 Simmons’ home at 513 East Railroad (later Norfolk) Street, hard by the tracks and in the shadow of a lumberyard. Page 14, 1922 Sanborn fire insurance maps, Wilson.

In the 1922 Hill’s Wilson, N.C., city directory: Simmons Olivia (c) cook h 513 Railroad. Here, we see the street has finally received a name, but, confusingly, there was already a Railroad Street in Wilson, running on the southeast side of the A.C.L. railroad.

In the 1925 Hill’s Wilson, N.C., city directory: Simmons Olivia (c) cook h 518 [sic] S Railroad

In the 1928 Hill’s Wilson, N.C., city directory: Simmons Olivia (c) laundress h 513 E Railroad

In the 1930 Hill’s Wilson, N.C., city directory: Simmons Olivia (c) cook h 513 E Railroad

In the 1930 census of Wilson, Wilson County: on Norfolk & Southern Street, in a home owned and valued at $1000, widow Olivia Simmons, 59, private cook; roomer Estella Jones, 29, laundress, and her children Olivia, 11, and Clarence Jones, 9; relative Rosa Simmons, 25, tobacco factory laborer; and daughter Reta Simmons, 15. (Another name change, to Norfolk & Southern Street, which was soon shortened to its present-day name — Norfolk Street.)

In the 1940 census of Wilson, Wilson County: at 513 Norfolk Street, Olivia Simmons, 72, cook; daughter Estella Jones, 45, laundress; grandchildren Olivia, 22, and Clarence, 20, both tobacco retrying factory laborers; and great-grandson Serevantly Jones, 9.

Olivia Simmons died 24 April 1952 at her home at 513 Norfolk Street, Wilson. Per her death certificate, she was born 4 December 1872 and was a widow. Rosa Simmons was informant.