The article on the basis of theoretical generalizations considers the main aspects of the development of the system of professional training of the future specialists of the transport industry in educational institutions of Ukraine in the late XIX – early XX centuries.The retrospective analysis of the development of professional training of the future specialists for the transport industry in Ukraine in the late XIX – early XX century was conducted on the example of the most progressive and highly paid at the time specialties in this sphere, namely: training of maritime specialists and railway workers.We found out that the period of the end of the XIX – 1917 is the time of creation of educational institutions for the training of the future specialists in maritime affairs. Thus, in the late XIX – early XX century there were more than 20 educational institutions in Ukraine, which provided training for the future sailors for the military and commercial fleet in the Black Sea. During this period, one of the key links in vocational education were maritime schools and long-distance sailing schools, in particular in the Kherson province, they were located in the cities of Beryslav, Oleshky and Hola Prystan, as well as Kherson. It is generalized that in the period of 1921–1941 the professional training of the future specialists for the fleet was done in corps (schools), in which the priority direction of professional training was defined as wide universalization.It is generalized that the development of railway transport took place in connection with the construction of the Kursk-Kharkiv-Azov railway in Slobozhanshchyna, which in turn needed qualified specialists of various professions who somehow interact with this industry. As a result, Kharkiv, an important railway junction, soon became a training center for the future railway specialists. Therefore, on December 1, 1870 at the station of Kharkiv opened a railway school for the training of technicians, which was reorganized into the Kharkiv Technical Railway School. In 1917, the Kharkiv Technical Railway School was reorganized into a Secondary Railway Vocational School. On its basis in 1921 the Kharkiv technical school of ways of a combination of a mechanical specialty with a four-year course of training was created.On its basis in 1921 the Kharkiv technical school of ways of connection of the mechanical specialty with a four-year course of training was created.In 1920, the Operational Technical School for the training of operational specialists was opened at the Southern Railway.On April 1, 1926, specialist training courses for engineers began to function in Kharkiv. On August 17, 1927, they were renamed into the Higher Technical Courses of the People’s Commissariat of Railways in Ukraine.In 1929, three railway technical schools (Technical School of Mechanical Railways, Operational Technical School and Evening Workers’ Mechanical Technical School) were merged into one professional technical institution - Kharkiv United Technical School of Railways.In the late 1920-s – early 1930-s the economy of the USSR gained momentum, but the transport industry did not keep up with the high rate of industrial development. Therefore, on March 23, 1930, the Kharkiv Institute of Railway Engineers began its work. Already in 1940–1941 academic year it became one of the largest railway institutions of higher education in the USSR.Thus, the retrospective analysis of the activities of educational institutions that provided training for the future transport professionals showed that during the period (late XIX – early XX century), in connection with the development of scientific and technological progress in society there was a need to train qualified future maritime specialists and railway workers. During this period, educational institutions were established, which actively developed in the system of professional training of transport specialists.