Charlottesville Union Station

Rose Cottage/Peyton House is a historic home located at Charlottesville, Virginia. It was built in 1856, as a simple three-bay, single-pile, two-story rectangular frame dwelling. The house is sheathed in weatherboard. Later 20th century additions include a single story Colonial Revival porch; matching one-story, one room wings; and a two-story, perpendicular house joined by and enclosed porch.It was listed on the National Register of Historic Places in 1983, and was removed from the National Register in 2017.

Peyton–Ellington Building is a historic commercial building located at Charlottesville, Virginia. It was built in 1893, and is a two-story, three-bay, brick building with an iron front facade. The facade features decorated pilasters at each end that support a cornice with a plain frieze, modillions, and cornice stops.It was listed on the National Register of Historic Places in 1982.

Delevan Baptist Church, also known as First Baptist Church and First Colored Baptist Church, is a historic African-American Baptist church building located at 632 W. Main Street in Charlottesville, Virginia. It was built in 1883, and is a one-story, three bay by six bay, Victorian Romanesque style brick church. It sits on a raised basement and features with a square projecting central tower topped by a large octagonal lantern on a square base, both of wood.It was added to the National Register of Historic Places in 1982. It is located in the Fifeville and Tonsler Neighborhoods Historic District.

Fifeville and Tonsler Neighborhood Historic District is a national historic district located at Charlottesville, Virginia. The district encompasses 264 contributing buildings and 3 contributing sites in a predominantly African-American residential section of the city of Charlottesville. It was developed between 1890 and the 1930s and includes examples of the Bungalow and Gothic Revival styles. The oldest is dated to 1822. Located in the district are the separately listed Oak Lawn, Benjamin Tonsler House, Delevan Baptist Church, and Gardner-Mays Cottage.It was listed on the National Register of Historic Places in 2009.

WKAV (1400 AM) is a contemporary Christian formatted broadcast radio station licensed to Charlottesville, Virginia, serving Charlottesville and Albemarle County, Virginia. WKAV is owned and operated by Monticello Media.

Hotel Gleason/Albemarle Hotel, Imperial Cafe is a historic hotel and commercial building located at Charlottesville, Virginia. It was built in 1896, and has a three-bay, three-story pressed-brick facade raised above the ground-floor recessed loggia in the Late Victorian style. The loggia is supported on four Corinthian order columns. The hotel closed in 1976.It was listed on the National Register of Historic Places in 1983.

The West Main Street Historic District encompasses a late 19th and early 20th century commercial area of Charlottesville, Virginia, developed during the area's growth as a streetcar suburb. It is basically linear in character, extending along West Main Street from Ridge Street in the east to the railroad crossing west of 8th Street in the west. The oldest building in the district is the c. 1820 Inge's Store, and the district includes the city's memorial to Meriwether Lewis and William Clark.The district was listed on the National Register of Historic Places in 2017.

Benjamin Tonsler House is a historic home located at Charlottesville, Virginia. It was built in 1879, and is a two-story, stuccoed frame Late Victorian dwelling with elements of the Italianate and Second Empire styles. It has a rear wing, high-pitched gable roof, and a projecting corner tower with a mansard roof.It was listed on the National Register of Historic Places in 1983. It is located in the Fifeville and Tonsler Neighborhoods Historic District.

Paxton Place is a historic home located at Charlottesville, Virginia. It was built about 1824, and is a 2+1⁄2-story, four-bay, Federal style brick dwelling. It has a side gable roof and two interior chimneys connected by a curtain. The house has been occupied by the Shisler Funeral Home and the Loyal Order of Moose Lodge.It was listed on the National Register of Historic Places in 1982.

Patton Mansion is a historic home located at Charlottesville, Virginia. It was built in 1907, and is a two-story, five-bay, double pile, Jeffersonian Revival Style brick dwelling. It has a hip roof and a full-height Tuscan order portico covering the center three bays of the front façade. There is a small hanging balcony with Chinese Chippendale baluster above the entrance.It was listed on the National Register of Historic Places in 1982.

Trax, later known as Crossroads, was a nightclub in Charlottesville, Virginia most notable for being a frequent gig for Dave Matthews Band during their early years. The band first played at the club a few months after forming in 1991. Because their local and regional popularity grew, they secured a standing gig at every Tuesday night from late 1992 through the end of 1993. The band became a national touring act on the verge of mainstream stardom by early 1994, so they only played at the club four times after 1993. Trax was featured briefly in the 1991 movie True Colors.Trax originally was an industrial building adjacent to the CSX train tracks (thus the name). When it changed hands in the early mid-1990s, it was briefly known as Crossroads. The building also housed a country and western nightclub called Max. The complex was located along 11th Street SW near the University of Virginia and also included John Hornsby's original Music Resource Center for kids. With a capacity of around 900 people, Trax played host to John Prine, Arlo Guthrie, Bill Monroe, Taj Majal, Cinderella (band), Seven Mary Three, Juliana Hatfield, Widespread Panic, Sun Ra, George Clinton, Ziggy Marley, 311, Sonic Youth, Mudhoney, Pavement, My Bloody Valentine, They Might Be Giants, The Pixies, The Ramones, Public Enemy, De La Soul, The Black Crowes, Southern Culture on the Skids, Phish, Shawn Colvin, and other popular acts. Before Ratdog, Bob Weir of the Grateful Dead and Rob Wasserman played there as part of a Native American benefit organized by musician Pete Sears. The benefit also featured Jorma Kaukonen, Michael Falzarano, Pete Sears, Chris Whitley and Dave Matthews. But after the rise of the legal drinking age and the decision by operator Coran Capshaw to spend more time with Dave Matthews Band, whom he managed, the venue fell into a slump. It was taken over by David Fisher in the early nineties for a brief period and then experienced a resurgence under Dana Murphy in the mid nineties, nurturing an ever growing music scene at the time. Earth to Andy frequented the club as well as My Dog Lucy, whose former guitarist would later join Daughtry. Trax closed around the middle of 2001 and was demolished at the end of the following year.

The Jefferson School is a historic building in Charlottesville, Virginia. It was built to serve as a segregated high school for African-American students. The school, located on Commerce Street in the downtown Starr Hill neighborhood, was built in four sections starting in 1926, with additions made in 1938–39, 1958, and 1959. It is a large two-story brick building, and the 1938–1939, two-story, rear addition, was partially funded by the Public Works Administration (PWA).This building operated from 1926 to 1951 as Charlottesville's first high school for Black students. In 1951, it became an elementary school for Black students. In 1958, Jefferson School students sought application to local white-only schools, sparking the city government to join the statewide massive resistance movement against school integration. After serving many uses over the following decades, it reopened in 2013 as the Jefferson School City Center, a multi-use facility that houses the Jefferson School African American Heritage Center, the Carver Recreation Center, and local community organizations.