In today’s society, the ability to think critically is crucial for success in both professional and everyday life. This paper presents a correlational study exploring the relationship between the frequency of playing modern board games (BG) and video games (VG), and critical thinking (CT) proficiency, addressing a gap in current research. Data were collected from 36 attendees of a major BG festival in Portugal using the Critical and Creative Thinking Test (CCTT), validated for the Portuguese population. The results suggest that while there was no statistically significant correlation between VG playing frequency and CCTT scores, positive correlations were found between BG playing frequency and the CCTT global score (p = 0.004), as well as the CCTT scores for interpretation (p = 0.002), analysis (p = 0.049), and explanation (p = 0.020). BG playing frequency was a predictor of these four variables (p = 0.004, p = 0.002, p = 0.041, p = 0.047, respectively). Additionally, age was negatively correlated with both BG playing frequency (p = 0.015) and CT proficiency in explanation (p = 0.007) and creation/production (p = 0.043). Further research is needed to identify the specific BG components that improve and predict CT proficiency and to understand the role of modern BG in lifelong learning and active aging.