Background: One of the fundamental challenges for gerontological research is how to maintain and promote intact cognitive functioning in old age. Previous research revealed that high educational level, good health status, and an active lifestyle during adulthood seem to be protective against cognitive impairment in old age. However, up to now, a de- tailed examination of the interaction of these relations based on a broader variety of activities and considering past and current activities is missing. Objective: The present study set out to extend the literature by investigating in more detail the interactions of educational level and health status with a broad variety of past and current leisure activities in their association with cognitive functioning in a large sample of older adults with a wide age range. Methods: A total of 2,812 older adults (aged 65–101 years) served as the sample for the present study. A test on verbal abilities and one on process- ing speed were applied. In addition, individuals were retrospectively interviewed regarding their educational level, current general health status, and 18 leisure activities (in terms of currently performed activities and those that had been carried out at the age of 45 years). Results: Regressions indicated that engaging in more current activities and in more activities at the age of 45 years (both analyzed as an overall activity measure) was related to better cognitive performance in old age (r values up to 0.39, p values <0.001). These associations were more pronounced in individuals with a low (compared to a high) educational level. Conclusion: Present results suggest that an active lifestyle during middle adulthood may be related to better cognitive functioning in old age, particularly in individuals with a low educational level. These findings are discussed with respect to models of cognitive aging.