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The Bar Complex is a gay bar located at 224 East Main St. in downtown Lexington, Kentucky, United States. While the building has gone through various name changes, it is remembered as gay-friendly as early as 1939, it has been an openly gay bar since 1963. The bar is 18,000 square feet (1,700 m2) between its two floors, and includes three bars, a stage for drag shows, and a two-story tall disco-era dance floor.

The Kentucky Theatre is a historic cinema in downtown Lexington, Kentucky, United States, that first opened in October 1922. The building is currently owned by the Lexington-Fayette Urban County Government and leased to a non-profit that shows films and hosts concerts and events. The theater's schedule emphasizes foreign, independent, and art films, although more typical Hollywood movies are occasionally shown, as well. It is one of a few remaining movie palaces in the United States. Each summer, the Kentucky Theatre hosts a Summer Classics series, showing a different classic film each Wednesday throughout the summer. Most films in the series are paired as one-night double-features or shown with an accompanying cartoon. These also include performances by organists part of the Bluegrass Chapter of the American Theatre Organ Society, which include classic and modern pieces and a sing-along before the show.

World Trade Center (Lexington) (also known as Vine Center Tower) is a 17-story high-rise office building located at 301 East Main Street in the city settlement of Lexington, Kentucky. It was completed in 1982 and stands at a height of 233-foot (71 m).

First African Baptist Church is a Baptist church at 264-272 E. Short Street in Lexington, Kentucky. The congregation was founded c. 1790 by Peter Durrett and his wife, slaves who came to Kentucky with their master, Rev. Joseph Craig, in 1781 with "The Travelling Church" of Baptists from Spotsylvania, Virginia. First African Baptist of Lexington is the oldest black Baptist church in Kentucky and the third oldest in the United States; it is the oldest black congregation west of the Allegheny Mountains. In 1850 under its second pastor, it had more than 1,800 members, the largest congregation of any in the state. The nineteenth-century Italianate church was constructed in 1856; by 1861 the congregation at this building numbered 2,223 members. The church was listed on the National Register of Historic Places in 1986. Today the first African Baptist congregation worships at a newer church at 635 Price Road.

The Lexington Herald Building, also known as the Nunn Building, in Lexington, Kentucky, is a 4-story commercial structure designed by Leon K. Frankel of Frankel & Curtis and constructed in 1917 as headquarters of the Lexington Herald. F. Paul Anderson, dean of the College of Engineering at University of Kentucky, where Frankel was also a professor, consulted on the steel frame of the brick building. The building's ornamentation is minimal, and it includes a denticulated cornice above the fourth floor windows and a parapet. There is a gable in the parapet in the front center holds a decorative scroll displaying an "H" (for Herald). The building was added to the National Register of Historic Places in 1982.John L. Nunn purchased the Lexington Herald in the 1930s, and the Lexington Herald Building is now more associated with Nunn than with the Herald. The building functioned as office space for various clients until 2006, when it was renovated and expanded as a condominium development.The building address had been 121 North Walnut Street, but Walnut was renamed Martin Luther King Boulevard, and the address is currently 121 N Martin Luther King Blvd.

Lexington Union Station was a union station, serving most of the railroads passing through Lexington, Kentucky. Located on Main Street, just west of Walnut Street (now, Martin Luther King Boulevard) it served the Chesapeake and Ohio Railway and the Louisville and Nashville Railroad from 1907 to 1957.

The Central Christian Church in Lexington, Kentucky, is a historic church at 205 E. Short Street, and an active congregation of the Christian Church (Disciples of Christ). The church was founded by Barton Stone and was the place where the Stone and Campbell movements united to form in 1832 as part of the Restoration Movement. The church was previously known as Hill Street Christian Church and Main Street Christian Church. The current building is part of the U.S. National Register of Historic Places.

The Lexington Public Library opened in 1905 in Lexington, Kentucky. It incorporated the collection of the former Lexington Library Company (est.1801) and the former Transylvania Library (est.1795). Today the main location of the Lexington Public Library system is Central Library along East Main Street connected to Park Plaza Apartments. The Library's facade includes rose-colored granite, with large windows facing the street and Phoenix Park. A rotunda in the lobby, the focal point of the building, spans all five floors and houses the world's largest ceiling clock and Foucault pendulum, designed by Lexington sculptor Adalin Wichman. The rotunda also includes a frieze depicting the history of the horse in the Bluegrass. Included within the complex is the 138-seat Farish Theater, meeting rooms and an atrium reading lounge. An art gallery is located on the ground floor. One of the areas for researchers is the Central Library's Kentucky Room, which houses Kentucky census records and numerous other genealogy and local history resources. It also contains microfilm of the Lexington Herald-Leader, as well as its forerunners, the Lexington Herald and the Lexington Leader, along with other local newspapers. Central Library is complemented by five branch locations. The Northside Branch, located on Russell Cave Rd., replaced the previous Northside location in 2008. The Tates Creek Branch, located on Walden Drive just off Tates Creek Rd., replaced the Lansdowne Branch in 2001. The Eastside Branch, located on Blake James Dr. at Man o' War Blvd. and Palumbo Dr., replaced the Eagle Creek Branch in 2016. The Beaumont Branch, located on Fieldstone Way just off Harrodsburg Rd., replaced the Southside Branch in 1997. The Village Branch, located on Versailles Rd. at Village Dr., opened in 2004. It boasts the distinction of being an English-Spanish bilingual branch, with bilingual staff.

The World Coal Center was a proposed skyscraper in Lexington, Kentucky where the Phoenix Hotel had once stood at South Limestone, East Main Street and East Vine Street. The $100.5 million project would have included the 41-level skyscraper and a retail shopping center. It is today home to the main branch of the Lexington Public Library, Park Plaza Apartments and Phoenix Park.

The Lexington Transit Center is a two-story public transportation facility utilized by Lextran and other regional transit services with a five-story underground parking garage along East Vine Street and East High Street east of South Limestone in Lexington, Kentucky. It features twelve bus stalls on E. Vine Street, four bus capacity on E. High Street, two indoor waiting rooms with restrooms and vending, and three clerk booths for ticket sales and customer service, with buses running every 35 minutes for much of the day. Completion of the transit center occurred in 1990 and was completed in conjunction with the Harrison Avenue (now Martin Luther King Drive) viaduct reconstruction.

Park Plaza Apartments is a 202 unit 21 story residential high-rise in Lexington, Kentucky. It is located between Main and Vine Streets at South Limestone, and is adjacent to Phoenix Park. The complex features a 425-space seven story parking structure, with residential units beginning at the eighth floor. It is connected to the Lexington Public Library.The apartment structure at 120 East Main features an exercise room on the eighth floor, although most of the equipment is broken.

The Phoenix Hotel was a historical structure located on East Main Street in Lexington, Kentucky, United States. It was established in the 1820s and became a prominent landmark as well as the oldest hostelry by succession in the area. After several reincarnations, the hotel closed in 1977. The building was demolished in 1987 and replaced by Phoenix Park.