Each organization fosters its own culture that is established, maintained and redeveloped in formal and informal social relations among co-workers; however, these are also influenced by the broader cultural environment in which a given organization exists. The question raised in this article is how the context of urban culture is reflected in the community of colleagues. We suppose that it is during such informal gatherings or during leisure time, when they can communicate more freely, and celebrate or mark various occasions that the social and cultural context of co-workers becomes apparent. The article aims to compare cultural expressions in co-workers’ communities among the inhabitants of Vilnius and Sofia by revealing the place of Soviet-period and current celebrations among co-workers. It also aims to show how an employee experiences his or her personal life cycle in a coworker’s environment, including (1) work-related personal events as the first salary, marking the length of service, retirement, and family-related events such as birthdays, weddings, and funerals, and (2) official holidays (public holidays, religious and other calendar feasts, commemorations of important dates, and other celebrations significant for the public). The study showed that the civil rites created in the Soviet era to promote coworkers’ participation were integrated into the culture of the urban people, by (1) transferring traditions of folk communities into the urban environment and in this way developing urban communities, and (2) allowing indirect control of the introduction of new holidays into the family environment. Comparing the expression of the cultural environment in coworkers’ gatherings among the inhabitants of Vilnius and those of Sofia, a difference was observed between the co-workers with regard to the family life cycle: in Sofia, coworkers very seldom socialize during funerals and only to some extent on the occasion of weddings, while the birth of a child is often marked in absentia, that is with the mother and the child absent. Meanwhile, the coworkers in Vilnius have always celebrated these occasions since the 1970s. As for the official holidays at the state level, Bulgarians, unlike Lithuanians, in Soviet times mentioned May 1 and national celebrations such as the Revival Leaders Day, the Saints Cyril and Methodius Day, and Baba Marta (Martenitsa), an informal one. This is apparently the reason why currently official celebrations enjoy greater popularity among coworkers in Sofia than among their counterparts in Vilnius. The first comparative studies of these cities show that a country’s official cultural policy influences the cultural expression of coworkers (and citizens in general): formal cultural expression is affected directly, and informal is influenced to some extent. When the end of the Soviet era heralded a new cultural policy, the intensity and intentions of formal holiday celebrations changed, but the character of informal celebrations remained more or less the same.