The COVID-19 pandemic and the obligation to wear surgical face masks have affected social interactions. Wearing a mask can cause impairments in face identification, emotion recognition, and trait impressions. The present study investigated, during the COVID-19 period, age-related differences in perceived trustworthiness (Study 1) and health (Study 2) when viewing faces with or without masks. Younger (YAs, 18–35 years) and older (OAs, over 65 years) adults’ ratings were compared. Through a web-based platform, a series of neutral younger and older faces (YFs vs. OFs) were presented, on a computer screen, with or without a mask (Mask vs. No-Mask), and participants were asked to rate them on a 7-point scale. Furthermore, data collected during the pandemic (Mask and No-Mask conditions) were compared with ratings obtained before it (Pre-COVID condition). Perceived trustworthiness was lower in the No-Mask condition for both age groups compared to Mask and Pre-COVID conditions, which did not differ. For health ratings, no differences emerged for OAs between the conditions, whereas YAs’ ratings were lower in both the Mask and No-Mask conditions compared to the Pre-COVID condition. The fear of contracting COVID-19 affected both trustworthiness and health ratings. Wearing a surgical face mask affects trait impressions for YAs and OAs, partly due to the fear of COVID-19. Trait impressions are also influenced by the age of the face to be evaluated.