This article deals with Soviet Estonian bicycle films focusing on sport. Four films are selected for analysis: three documentaries by Hans Roosipuu and the fiction film Kuljetuul/Side Wind (1983) by Raul Tammet. The films show a chronological development of the bicycle race film, starting with Hans Roosipuu’s short film Ulekanne 56:13/Transmission 56:13 (1969) and ending with Raul Tammet’s Side Wind, screened on television a few years before Glasnost was introduced in the Soviet Union. The analysis focuses on the issue of national identity building on the notion that sport was one of the few venues where Estonians could express their nationality. The analysis finds that the closer we get to the Glasnost period the more the films tend to highlight the Estonianness or concerns for Estonian bicycle riders. Moreover, in comparison with Western bicycle film, the Estonian films have didactic qualities based in the traditions of socialist realism and a tendency to elevate the bicycle race mechanic due to Soviet bicycling culture being less advanced. Also earlier than their Western counterpart, the Estonian bicycle films are concerned with the ‘green’ value of the bicycle in a drive to criticize the Soviet authorities. In doing this the Soviet Estonian bicycle films adheres to the dynamic of the Glasnost film.