The square is located on the Garden Ring and is approached by six streets. The first mention of the square dates back to 1592-1593, when the Earth Wall was built, protecting the Earth City from invasions. This was Moscow's fourth fortress wall.

Just behind the Kaluga Wooden Gate, the new square is located. In 1640, the gate was made of stone. Just once in their lives, they repelled the attack of the invaders — the Polish troops, who stormed the capital in 1618. Then the Russian soldiers managed to defend their land.

At the end of the 17th century, shopping arcades were built on the square and the active sale of hay, oats, bread and firewood began. Since the 18th century, there has been a “zhitny yard” here, in which grain reserves are stored. Later, the cattle market was moved here.

Kaluga prison is being built not far from the shopping arcades, which will stay here until 1785, and then move to Butyrskaya prison.

In the 18th century, the square was rebuilt for the first time, and a stone chapel and butchers appeared on it. In 1812, wooden houses on the north side of the square burned down in a fire. The southern side remains intact — French troops leave the capital along it through Kaluzhskaya Square.

The next century is again marked by the reconstruction of the square: it is being expanded and two-story stone houses with benches on the first floors and living quarters on the second floors are being built. That's when the square looks like a frying pan because of its round shape.

Many buildings have an interesting history here, for example, the Poltoratsky estate was bought by a community of merchants, St. Andrew's Almshouse for 100 people was opened in it, and in 1836 it settled here The Bourgeois School, seven years later, is another bourgeois school, this time for girls.

A sadder fate befell the Church of the Icon of the Kazan Mother of God, built in 1882. In the 30s of the XX century, it was used as a cinema, and in 1973 it was completely demolished. Now the Ministry of Internal Affairs building stands on the site

At the beginning of the 20th century, the market was closed and a square with a fountain was laid out in its place.

In 1922, the square was renamed Oktyabrskaya Square. Thus, for some time in Moscow there are two squares with the same name. In 1950, the first metro station, Oktyabrskaya, appeared here.

In the middle of the 20th century, the square was once again changed, as a result of the reconstruction of the Garden Ring, a six-lane tunnel was laid under the square.