The COVID-19 pandemic emergency has challenged children’s socio-affective and cognitive development. It is essential to capture the modulation of their emotional experience through ecological and children-friendly tasks, such as written narratives and drawings. This contribution investigates the impact of pandemic experience (2020–2021 waves) on the internal states and emotions of the primary school age children, according to a longitudinal research approach through narratives (study 1 n = 21) and drawing tasks (study 2 n = 117). 138 Italian children were examined during COVID-19 three (study 1) or two waves (study 2). Children’s written narratives were codified on the basis of narrative competence and psychological lexicon. Children’s drawings were codified based on social/emotional, physical, and environmental elements. Results of narrative texts showed a lower psychological lexicon relating to positive emotions and a greater psychological lexicon relating to negative emotions only in the study sample group during the first lockdown compared to the previous and subsequent periods. Children’s drawings of themselves showed a decrease of negative emotions during the third pandemic wave in comparison to the first pandemic wave. Results inform mental health services, school practitioners, and parents about the importance of written narratives and drawings for promoting well-being in the developmental age.