Updated: Sep 25
When Denison, Texas was born in 1872, it did not have much of anything save for a railroad track. But this track led into Indian Territory and Missouri, which meant that the city was, for a while, the terminus for all points north. And this created a boom town. As more railroads built into Denison to connect to interstate traffic, the city prospered beyond anyone's wildest dreams.
With this flash of wealth and opportunity came many immigrants and migrants. Because the city grew so quickly and without much planning, a vice zone appeared, organically, just south of Main Street and just west of the tracks along Skiddy Street. Ultimately, this saloon and brothel quarter had at least three establishments dedicated to vice. The most notorious brothel in Denison was Brown Front, named so because it, well, had an unpainted wooden front that was none too pretty.
Not too happy with the idea of vice so close to Main Street, city leaders decided to rename Skiddy to the more genteel "Chestnut Street" in the hopes of confusing visitors. It also placed its jail in the same vicinity as the Brown Front. When the Brown Front burned in 1880, the respectable people of Denison rejoiced; when two women, K. Ulch and Mollie Newton, rented and re-opened the Brown Front to continue its business, Denison seemed to despair.
The quarter became a haven for crime, with many murders and attempted killings inside the "female boarding houses," as brothels tended to be labeled on Sanborn Maps. However, when tragedy struck the district, the entire city of Denison rallied around the women who lived there. In 1892, Dick Edwards alias Billy Leroy went on a rampage on Skiddy Street, shooting several of the female residents and killing four (I've also read that three were killed and a fourth injured). Called "the horror at Denison," the women victims were offered sympathy and assistance. The perpetrator was convicted, and the vice district became a bit more subdued, but ultimately only succumbed to the bulldozer during the moralistic, progressive-era clean-ups of the early 20th century.
Vice did not leave the city, however. Prostitution and drinking just went "underground" and blended with the hotels further west on Main and Chestnut streets. The town also had several "speakeasies" (places that served liquor during prohibition). The last speakeasy in Whitewright, Grayson County (a neighboring town) actually closed shop in the 1990s... it still had no legal right to serve alcohol in a town with local ordinances that insisted it was "dry."
Today, Chestnut Street, aka Skiddy Street, houses more parking lots than Brown Fronts, and is only alive in the stories told.