The study focuses on the Ukrainian generation of the Thaw known as “the Sixtiers”. Gradual development of their worldview is mapped on the examples of their reflections on crucial political and cultural events that took place during the Thaw from 1953 till 1965 and formed the historical experience of the younger generation during the defined period. The article is concentrated on five key events: Stalin’s death in 1953, the Secret speech in 1956, the Kurenivka tragedy in 1961, the fire in Public library in Kyiv in 1964 and the mass arrests of Ukrainian intelligentsia in 1965. The reflexion of the Sixtiers on these events is traced according to their diaries, letters, published texts and recorded interviews. The study also maps the approaches of the Soviet officials during these events that are shown with a help of archival KGB files. On the basis of these sources the article maps gradual development of the worldview of the Sixtiers and their shift from relatively loyal Soviet citizens to opposition minded intellectuals and dissidents.