Holosiivskyi Prospect, one of the city’s main transport arteries, runs along the entire northwestern edge of M. Rylskyi Park. Its historical roots trace back to the times of Kyivan Rus', when it was a quiet forest road connecting Kyiv to the Holosiiv Monastery. The avenue's major development began in the late 19th century, with the first residential buildings appearing in 1958. 

Over time, the avenue has been expanded and modernized, with new buildings replacing old ones. Today, across from the park’s green zone, you can see a mix of archaic private estates, Soviet-era constructivist structures, and modern high-rise residential complexes. 

Notable architectural landmarks along Holosiivskyi Prospect include the gates of the Demiivskyi projectile factory, the complex of buildings from the 19th-century Schultz Demiivskyi brewery, the former Baryshpolskyi Synagogue, the Voznesenska Church, and a century-old fire station. Despite all the changes, the avenue has retained its unique charm and remains one of the most picturesque parts of Kyiv.