During the late 18th century, Madrid was surrounded by medieval walls and lacked aesthetic appeal. In 1774, King Charles III tasked Francesco Sabatini with constructing a grand gate that would serve as the entrance to an expanded road leading to the city of Alcalá. The gate was completed in 1778 and is known for its ornamental details, which were sculpted by Francisco Gutiérrez and Roberto Michel, and constructed using white stone from Colmenar. The architectural elements, on the other hand, were made from granite sourced from Segovia.
The Puerta de Alcalá endured cannon shrapnel, leaving visible marks that remain to this day.
In 1854, following his defeat at Vicálvaro, the Count of Villahermosa paraded through Madrid with the spear of an enemy soldier, earning him the sarcastic nickname "Longinos" from the Madrileños.
On March 8, 1921, Eduardo Dato, the Prime Minister of Spain, was shot and killed by three Catalan anarchists driving a motorcycle with a sidecar while driving home through Plaza de la Independencia after a long parliamentary session.
The Puerta de Alcalá was once a route for seasonal livestock migration, and flocks of sheep frequently crossed through the square, but this practice is no longer in use.
In 2001, the Puerta de Alcalá underwent a transformation to celebrate Madrid being named the "Capital Mundial del Libro" (World Book Capital), with the addition of gardens and night lights.
The song "La Puerta de Alcalá" by Ana Belén and Víctor Manuel became one of their greatest hits in 1985, named after the monument.
During the 2010 MTV Europe Music Awards, Thirty Seconds to Mars, Katy Perry, and Linkin Park performed live from the Puerta de Alcalá in front of nearly 100,000 fans.
Mexican singer Anahí and Spanish singer David Bustamante have also covered "La Puerta de Alcalá," included in Anahí's sixth album, Inesperado.
Finally, the closing ceremony and concert of WorldPride 2017 took place at Puerta de Alcalá on June 2, 2017.