A travel route generation apparatus includes a work field data input interface, a handwriting input interface, a memory, and circuitry. Work field data are to be input via the work field data input interface. The work field data includes data regarding a shape of a work field in which a work vehicle is to work. A handwriting locus is to be input via the handwriting input interface. The memory is to store travel route patterns. The circuitry is configured to select a designated travel route pattern from travel route patterns based on the handwriting locus and to generate, based on the designated travel route pattern and the work field data, a travel route along which the work vehicle is to travel in the work field.