The present study analyzed the relations between the Big Five personality traits (neuroticism, extraversion, agreeableness, conscientiousness, and openness to experience) and 14 values (societal concern, tolerance, protecting nature, caring, dependability, autonomy of thought, autonomy of action, stimulation, hedonism, achievement, tradition, security, conformity, and power) in middle-aged women and men. The 50-year-old participants (women n = 107 and men n = 105) were drawn from the ongoing Finnish Jyväskylä Longitudinal Study of Personality and Social Development. The personality traits were assessed using the 60-item NEO Five Factor Inventory. Values were measured using the 46-item version of the Schwartz Value Survey. The multi-group regression model confirmed that openness to experience, agreeableness, extraversion, and conscientiousness moderately explained 10 of the 14 values. Among both genders, the most consistent positive association was found between openness to experience and autonomy of thought and the most consistent negative relation was found between openness to experience and power. Statistically significant gender differences were found in three positive relations: agreeableness contributed to tolerance in men, whereas openness to experience was related to autonomy of action and conscientiousness to achievement in women.