This paper analyses the transformation of commercial facilities and transport system in Pelhrimov - a town with heritage protected centre. We focus on the period from the socialist to the post-socialist era. We analyse the position of the commercial facilities within the town, their relationship to the transport system and the spatial boundary between the public space and the buildings. The subject of analysis are the archive documents comprising the land use plans and accompanying reports. The results show the close relationship between the historic centre, the market, and the transport until the second half of the 20th century. The socialist planning operates with the land use maps, cancels the concept of a street and separates different functions of the settlements. Consequently, the commerce facilities are separated from the main transport routes. The socialist centrally-planned system allowed demolitions of parts of historical towns and a subsequent development of large scale department stores. The post-socialism era reintroduces the concept of a street and talks about humanisation of the former transport routes. Nevertheless, the new streets do not follow the traditional street typology with close contact between the passers-by and the commercial activities in buildings. Instead, it introduces large-scale commercial centres with spacious parking lots, accessible mainly by cars.