Lexington is the second-most-populous city in the Commonwealth of Kentucky (after Louisville), and the 60th-most populous city in the United States. Lexington is known as the "Horse Capital of the World". 

It is within the state's Bluegrass region. Notable locations within the city include the Kentucky Horse Park, The Red Mile and Keeneland race courses, Rupp Arena, Central Bank Center, Transylvania University, the University of Kentucky, Bluegrass Community and Technical College, and the National Thoroughbred Racing Association (NTRA) Headquarters.

June has two popular music festivals: Bluegrass and Broadway. The Festival of the Bluegrass, Kentucky's oldest bluegrass music festival, is in early June; it includes three stages for music and a "bluegrass music camp" for school children. For more than two decades, during the second and third weekends, UK Opera Theatre presents a Broadway medley "It's A Grand Night for Singing!"

Later in June, the Gay and Lesbian Services Organization hosts the Lexington Pride Festival, which celebrates pride of the LGBTQIA+ community and welcomes allies. The festival offers live music, crafts, food, and informational booths from diverse service organizations. Lexington Mayor Jim Gray, elected in 2010 and openly gay, proclaimed June 29, 2013, as Pride Day. Lexington has one of the highest concentrations of gay and lesbian couples in the United States for a city its size.

Area residents gather downtown for the Fourth of July festivities, which extend for several days. On July 3, the Gratz Park Historic District is transformed into an outdoor music hall, when the Patriotic Music Concert is held on the steps of Morrison Hall at Transylvania University. The Lexington Singers and the Lexington Philharmonic Orchestra perform at this event. On the Fourth, events include a reading of the Declaration of Independence on the steps of the Old Courthouse, a waiters' race in Phoenix Park, a parade, a country-music concert, street vendors for wares and food, and fireworks. The Woodland Arts Fair is almost four decades old.

"Southern Lights: Spectacular Sights on Holiday Nights", which takes place from November 18 to December 31, is held at the Kentucky Horse Park. It includes a three mi (4.8 km) drive through the park, showcasing numerous displays, many in character with the horse industry and history of Lexington. The "Mini-Train Express", an indoor petting zoo featuring exotic animals, the International Museum of the Horse, an exhibit showcasing the Bluegrass Railway Club's model train, and Santa Claus are other major highlights.

Other events and fares include:

The North Limestone (NoLi) Night Market
The Lexington Philharmonic Orchestra presents several annual concerts.
The Lexington Ballet Company performs their annual Nutcracker Ballet.
LexArts Gallery HOP is a seasonal event when the city's art galleries are open to the public on the third Friday of January, March, May, July, September, and November.