Usually urban themes are not to be anticipated in older Estonian folk song.This is, firstly, because the songs presumably date back to more than two thousand years. Secondly, the background and typical themes refer regilaul to an agrarian culture. The tradition of singing in regilaul style receded from active use after the mid-19th century, with the advance of extensive changes in the economy, education and population behaviour in the present-day Estonian territory. At a closer look, however, some figures involving town names as well as mentions of urban themes can be observed. In Estonia, the first townships emerged in the 13th and 14th centuries, developing into towns in the Late Middle Ages. For village people a town meant, first and foremost, a trading place. Etymologically the Estonian word linn ’town, city’ refers to a stronghold or citadel, which is also manifested in the songs where ‘town’ is associated with ‘stronghold’, metaphorically referring to protection of parents and family. The article analyses the town names and urban themes occurring in regilaul. The approach is based on social history, asking to what extent the songs might reveal the everyday life and attitudes of the villagers of the time. The first part of the study is focused on formulas, i.e. on alliterative phrases, where a town name is included, e.g. Riia – rikas ‘rich’; rist ‘cross’; Narva – naine ‘woman, wife’ ; Lihula – linna ‘citadel’. The second part analyses the town-bound attitudes manifested in the songs. There are three major urban themes: the rituals and procedures leading to a marriage proposal, trade, and recruitment of soldiers. Migration from villages to towns is less elaborated. In most cases it has to do with job search, while urban work and lifestyle are considered easier than the rural ones. A wife wedded from town is a theme arousing markedly contradictory attitudes, but the image of the town woman as one with low morals is dominating. Bringing down goods from the town, however, was usual and town goods were appreciated.