Emerging evidence suggests that atypical changes in driving behaviors may be early signals of mild cognitive impairment (MCI) and dementia. This study aims to assess the utility of naturalistic driving data and machine learning techniques in predicting incident MCI and dementia in older adults. Monthly driving data captured by in-vehicle recording devices for up to 45 months from 2977 participants of the Longitudinal Research on Aging Drivers study were processed to generate 29 variables measuring driving behaviors, space and performance. Incident MCI and dementia cases (n = 64) were ascertained from medical record reviews and annual interviews. Random forests were used to classify the participant MCI/dementia status during the follow-up. The F1 score of random forests in discriminating MCI/dementia status was 29% based on demographic characteristics (age, sex, race/ethnicity and education) only, 66% based on driving variables only, and 88% based on demographic characteristics and driving variables. Feature importance analysis revealed that age was most predictive of MCI and dementia, followed by the percentage of trips traveled within 15 miles of home, race/ethnicity, minutes per trip chain (i.e., length of trips starting and ending at home), minutes per trip, and number of hard braking events with deceleration rates ≥ 0.35 g. If validated, the algorithms developed in this study could provide a novel tool for early detection and management of MCI and dementia in older drivers.