The first information about Trubnaya Square dates back to the 14th century, at the same time the foundation of the Rozhdestvensky Convent and Sretensky Monastery was laid. The construction of the outer side of the square, where the monastery arable land was located, began in the 16th century. The territory bordering the monasteries began to be gradually populated and after a while, the settlement of the Pechatny Dvor was founded in this place.

After the walls of the White City were demolished in 1760, spontaneous construction of various retail outlets began on the site of the current Rozhdestvensky Boulevard. During the monstrous fire of 1812, almost all the buildings that were located on the outside of the boulevard were destroyed by fire. Fortunately, the buildings located on its inner side have survived.

Since the second decade of the 19th century, the modern appearance of Rozhdestvensky Boulevard began to gradually form. It descended in the direction of Trubnaya Square, and at its end (at the Sretensky Gate) the foundation of the hotel was laid, which has survived on this place to this day. Today, there are many well-known buildings of historical value along Rozhdestvensky Boulevard. Among them are the Church of the Assumption of the Virgin, the Nativity Monastery of the Mother of God, as well as houses where famous citizens, literary and political figures once lived.