Ivan Mazepa Street is one of the oldest arteries of Pechersk, which arose on the site of the ancient Ivanovsky Way, which even during the times of Kyivan Rus’ people got from Podol to the Kyiv-Pechersk Lavra. Since the beginning of the 18th century, it was called Velyka Mykilska — from the Mykilsky Cathedral, which stood here until 1935. The Soviet authorities renamed it in honor of the armed uprising of 1918, and only in 2007 did the street finally receive the name of Hetman Ivan Mazepa. There is also one interesting geographical record here: in the courtyard of houses No. 4-b and 6 is the highest point of Kyiv above sea level — 196 meters.
The street is rich in architectural monuments of different eras. At the beginning is the Mykolaiv Gate of the Kyiv Fortress from 1846–1850, next to it is the famous “Airplane House” at No. 3 and the Ypsilanti estate from 1798. Next is the Kyiv Palace of Children and Youth, a monument of Soviet modernism. This street is like a synopsis of Kyiv history: from the medieval path to pilgrims – through Soviet renamings – to the return of the name of the hetman, whose portrait still adorns the “Eternal Kyiv” monument on Glory Square.