A travel route generation device is provided, the travel route generation device includes: an acquisition unit (21) that acquires field data including a field shape; a setting unit (22) that allows setting of a travel work parameter including headland information based on a manual operation; a generation unit (23) that generates a travel route R along which a tractor travels based on the field data and the travel work parameter; a route expectation unit (24) that derives route expectation information E about the generated travel route R; and a display control unit (25) that causes a display device (11) capable of displaying information to display the acquired field shape F, the generated travel route R, and the derived route expectation information E. Further, a method for operating a travel route generation device is provided.