Vinegar Hill, an early red-light and entertainment district in Houston, was located in the northwest corner of downtown on a wedge-shaped city block formed by the intersection of Washington and Preston avenues and bounded on the east by the Buffalo Bayou a few blocks south of the Central Railroad Depot. Tin Can Alley, the main thoroughfare that divided Vinegar Hill into two sections and ended at the east bank of Buffalo Bayou, was as legendary as the area itself. One Houstonian commented that “Tin Can Alley” was “the toughest place in the South.”
Vinegar Hill was established by the late 1860s. Local tradition holds that this area was dubbed Vinegar Hill because of the infestation of vinegaroon scorpions in the neighborhood. The name may also be in reference to the smells that eminated from the nearby vinegar factory. Regardless of where it originated, the name was meant to be repulsive and described its residents and the type of lawlessness that prevailed within its boundaries.
The whole area consisted of one and two-room box-shaped tenement houses and dilapidated shacks randomly scattered all over the land. There were no fences or definitive dividing lines between structures nor were there sidewalks except for worn pathways left by those who moved from house to house. The clusters of houses served as residences for African American women and children. Vinegar Hill had a strong criminal element that catered to gambling, prostitution, violence, and the sale of drugs. Although the area had a primarily black population, people of various ethnic groups and races engaged in unlawful activities. Vinegar’s Hill’s main business was a saloon located at the corner of Washington Avenue and 9th Street.
At the center of Vinegar Hill’s den of infamy was the legendary “Queen of Vinegar Hill”—Caroline Riley. Often called the “one-eyed terror,” Riley, a black woman who had arrived in Vinegar Hill about 1867 and had many run-ins with law enforcement, was regarded as intelligent but also “cunning” and “treacherous.” She ruled with an iron fist. According to Houston: A History and Guide, “Big Foot Jen, Charley Johnson, Lillie Rivers, and Julia Baker were her lieutenants.”7 When a Galveston Daily News reporter, writing about Houston’s “dark side,” visited the palace of Queen Caroline Riley in March 1874, he wrote that “her features as they were illumined by the light of an ordinary kerosene lamp, bore fearful record of years of dissipation, sin and crime.”
This news story, along with community complaints, possibly prompted law enforcement and firefighters at Mechanic 6 and Brooks 5 stations to begin the systematic clean up of Vinegar Hill. The “cleansing” included incidences of arson committed by some of the firefighters to “rid the Hill of one more shack,” as well as knocking down some rickety structures with the use of high pressure water hoses. When Caroline Riley died in April 1880, the area was sold at public auction the following year, on April 5, 1881, to make way for the expansion and improvements of the Houston and Texas Central Railroad. The reputation of Vinegar Hill gradually changed. By the 1920s, when the Tennison Hotel was built to accommodate arriving and departing train passengers, Vinegar Hill consisted of large and small factories and stores throughout the area. This commercialization continued into the 1950s. Once the demolition of Grand Central Station took place in the 1960s, the need for the Tennison Hotel dwindled until it closed in 1972.
In the 2010s the elevated overpasses of Interstate 45 and the Downtown Aquarium Houston were all that remained of Houston’s oldest entertainment district—Vinegar Hill.