In Japan, the amount of agricultural production decreases year-by-year. Moreover, reduction in agricultural work population and increase of abandonment of cultivated land are major social issues. To overcome these issues, we have proposed a small agricultural robot “MY DONKEY®” which supports transportation of harvested crops and records the farm work of the user and crop yield in field map while moving closer to the user. In order to move in the furrowed field, it is necessary to detect ridges and furrows where the robot can move using robot-mounted sensors and follow the ridge while avoiding the ridges and crop rows. Furthermore, to realize smooth harvesting support, we propose a ridge-tracking control according to user’s behavior based on the recognition of the work contents of the user such as harvesting, loading of harvested crops to the robot, transportation, and movement. We propose the ridge-tracking control framework based on fuzzy set theory which can evaluate and integrate multiple situations and carry out experiments in strawberry farm.