Visual self-expression helps with attention and improves health and well-being. Few studies have examined reward pathway activation during different visual art tasks. This pilot study is the first to examine brain activation via functional near-infrared spectroscopy (fNIRS) during three distinct drawing tasks—coloring, doodling, and free drawing. Participants (11 men, 15 women; 8 artists, 16 non-artists) engaged in each task separated by equal intervals of rest in a block design experimental protocol. Additional data included a pre- and post survey of self-perceptions of creativity, prior experience with drawing tasks, and reflections on study participation. Overall, the three visual arts tasks resulted in significant activation of the medial prefrontal cortex compared to the rest conditions. The doodling condition resulted in maximum activation of the medial prefrontal cortex compared to coloring and free drawing; however, differences between the drawing conditions were not statistically significant. Emergent differences were seen between artists and non-artists for coloring and doodling. All three visual self-expression tasks activated the medial prefrontal cortex, indicating potential clinical applications of reward perception through art making. Participants improved in their self-perceptions of problem solving and having good ideas. Participants found the drawing tasks relaxing but wanted more time per task. Further study with varied art media and longer time on tasks are needed to determine potential interactions between participants’ backgrounds and reward activation.