A drivetrain system is disclosed for use with a machine having a work tool. The drivetrain system may have a transmission with a plurality of clutches. The drivetrain system may also have an input device movable by an operator to generate a first signal indicative of a desired selection of a park setting or one of a plurality of travel settings, a sensor configured to generate a second signal indicative of loading of the work tool, and a controller in communication with the input device, the sensor, and the transmission. The controller may be configured to anticipate completion of a loading cycle based the second signal, and to selectively cause at least a first of the plurality of clutches to engage in a combination that produces one of the plurality of travel settings based on the anticipated completion of the loading cycle, notwithstanding the desired selection from the input device being the park setting.