Objective: We investigated cross-lagged relations between leisure activity participation and Trail Making Test (TMT) performance over 6 years and whether those reciprocal associations differed between individuals. Method: We analyzed data from 232 participants tested on performance in TMT Parts A and B as well as interviewed on leisure activity participation in 2 waves 6 years apart. Mean age in the Wave 1 was 73.42 years. Participants were also tested on vocabulary (Mill Hill scale) as a proxy indicator of crystallized intelligence and reported information on early and midlife cognitive reserve markers (education and occupation). Latent cross-lagged models were applied to investigate potential reciprocal activity TMT relationships. Results: The relation of leisure activity participation predicting TMT performance 6 years later was significantly larger than was the relation of TMT performance predicting later leisure activity participation. Statistically comparing different moderator groups revealed that this pattern was evident both in individuals with low education and in those with high education but, notably, emerged in only young-old adults (but not in old-old adults), in individuals with a low cognitive level of job in midlife (but not in those with a high cognitive level of job in midlife), and in individuals with high scores in vocabulary (but not in those with low scores in vocabulary). Conclusions: Late-life leisure activity participation may predict later cognitive status in terms of TMT performance, but individuals may markedly differ with respect to such effects. Implications for current cognitive reserve and neuropsychological aging research are discussed.