Vinegar Hill (originally known as Random Row) was a historically black neighborhood that was razed in 1964 as part of a Charlottesville-led redevelopment program. The neighborhood extended along Main Street from the eastern end of today's Downtown Mall.
The neighborhood was first settled by Irish families in the early 1800s and annexed by the City of Charlottesville in 1835. James Alexander, a newspaper editor who lived in Charlottesville in the 19th century, said the name Vinegar Hill was given to the neighborhood by George Toole in honor of his family home by the same name in Ireland. African American families first moved to the neighborhood following the Civil War.
Another account states that one day a barrel of vinegar fell off of the back of a truck and left the neighborhood reeking for some time. Another story is that "vinegar" was a code for liquor. 
The neighborhood became the center of the African-American community by the mid 1920's and was the home of many black-owned businesses. 
In 1960, Charlottesville voters approved a referendum authorizing the redevelopment of Vinegar Hill. A poll tax prevented many of the neighborhood's residents from participating in the vote. In a 1960 survey conducted by the city, 29 businesses in the Vinegar Hill neighborhood were determined to have a combined gross income of $1.6 million. The area was leveled in 1964. Many of the approximately 500 displaced residents moved into the Westhaven public housing project.
Since the redevelopment was completed, it has been a point of contention in local race relations. A short documentary film chronicling the neighborhood's founding, development, and demise premiered at the Vinegar Hill Theater as part of the 2010 Virginia Film Festival. In the film, Kathy Harris, who grew up in the neighborhood, noted that after the destruction of Vinegar Hill her classmates and siblings "could not find employment here," and that "there are just no opportunities here for African American people."
On December 6, 2016, City Council voted to allocate $15,000 for the establishment of a memorial plaza honoring Vinegar Hill at the western end of the Downtown Mall. The only existing marker on the site identifying the area as a boundary of Vinegar Hill was long obscured by a trash can.
The Vinegar Hill Monument Action Team of the Dialogue on Race is seeking to build a monument to the neighborhood on the grounds of the Jefferson School City Center and asked City Council in early 2012 for $24,000 from the Percent for Art fund to pay for its design. Council only gave $18,000 to the design stage. Construction is budgeted between $100,000 and $200,000. Three artists were in the running for the sculpture but Melvin Edwards of New York City was selected to create it.
Local Voices, Local History
| VIDEO CREDITS: Narrated by John Gaines and Ann Carter;|
Graphic design: Jen Fleischer; Project Manager: Kristin Rourke.
- Web. Vinegar Hill Monument Proposal, Dialogue on Race, Page 13, retrieved November 21, 2011.
- Web. Early Charlottesville: Recollections of James Alexander, 1828-1874, Jeffersonian Republican, Albemarle County Historical Society, 1942, retrieved 5 Aug 2013.
- Web. Vinegar Hill, City of Charlottesville, retrieved 5 Aug 2013.
- Web. Urban Renewal and the End of Black Culture in Charlottesville, Virginia: An Oral History of Vinegar Hill, James Robert Saunders and Renae Nadine Shackleford, Book, McFarland & Company, Jefferson, North Carolina, 1998, retrieved October 8, 2017.
- Book. [ Urban Renewal and the End of Black Culture in Charlottesville, Virginia], James Saunders and Renae Shackelford, 1st
- Web. Charlottesville officially apologizes for razing Vinegar Hill, Graham Moomaw, Daily Progress, World Media Enterprises, November 07, 2011
- Web. That World is Gone: Race and Displacement in a Southern Town, Field Studio, November 6, 2010, retrieved December 31, 2016.
- Web. Charlottesville City Council Allocates $15K to Create Vinegar Hill Park, Rachel Menitoff, NBC29, December 6, 2016, retrieved December 31, 2016.
- Web. Charlottesville Removes Trash Bin Blocking Vinegar Hill Plaque, Nora Neus, NBC29, August 12, 2016, retrieved December 31, 2016.
- Web. November 21, 2011 City Council Agenda, City of Charlottesville, Page 12, retrieved November 21, 2011.
- Web. City to vet possible designers for Vinegar Hill monument, Graham Moomaw, Daily Progress, World Media Enterprises, April 14, 2012, retrieved April 16, 2012.
- Web. Renowned sculptor selected to create Charlottesville's first commissioned work in decades, Graham Moomaw, Daily Progress, World Media Enterprises, April 29, 2012, retrieved May 1, 2012.