: Handwriting and Drawing are functional tasks involving physical and cognitive processes. Recently they have been investigated for detecting cognitive and motor disorders. In this work, handwriting/drawing features are investigated for identifying connections with personality traits. For this purpose, an experiment comprising seven handwriting/drawing tasks has been administrated to 78 young adults (mean age=24.6 ± 2.4 years) equally balanced by gender. Handwriting and Drawing activities - both on and close to the paper – had been recorded online through a digitizing tablet able to measure handwriting and drawing features such as pressure, speed, dimension, and inclination of each pen-stroke on the paper. Participants were asked to fill the Big Five Personality Questionnaire (BFQ) and according to the scores obtained for each of the 5 dimensions and 10 Big Five sub-dimensions, were partitioned into three categories: low, typical, and high. To evaluate whether the recorded handwriting/drawing features are connected with personality traits ANOVA repeated measures have been performed with gender and group category (low, typical, and high) as between and the listed handwriting/drawing features as within factors. The analyses show significant differences among low, typical and, high BFQ scores for the main Big Five dimensions and the ten Big Five sub-dimensions, indicating that personality traits can be revealed by a quantitative analysis of the proposed handwriting/drawing features.