One of the current scientific challenges is to propose novel tools and tasks designed to identify new motor biomarkers in Parkinson’s disease (PD). Among these, a focus has placed on drawing tasks. Independently from clinical ratings, this study aimed to evaluate the pen movement and holding in digitalized spiral drawing in individuals with PD without and with medical treatment and in healthy controls. A three-step data-driven analysis was conducted. First, the effects of spatial and temporal constraints on several variables were determined. Second, the relationship between handedness and dominance of PD symptoms was investigated for the most relevant variables. Finally, a third analysis was conducted to assess the occurrence of changes associated with PD. The first analysis revealed that the number of velocity peaks and pen altitude variations were the most relevant variables in spiral drawing for evaluating the effect of the disease and medication. The second analysis revealed that the effect of medication was present for the movement fluency only, when spirals with spatial constraints were produced at a spontaneous speed by the hand on the side of dominant PD signs. Finally, the third analysis showed that the effect of medication was greater at the beginning of drawing than at the end. Digitalized spiral drawing makes it possible to observe precisely when the kinematic changes related to the disease occur during the task. Such a simple and quick task might be of great relevance to contribute to the diagnosis and follow-up of PD.