Systemic safety analysis is a comprehensive and proactive approach to identifying and addressing high-risk roadway features and crash types that contribute to severe crashes. The Massachusetts Department of Transportation identified 14 emphasis areas for systemic improvement, including younger and older driver crashes. Research was undertaken to conduct separate comprehensive analyses of fatal and serious injury crashes involving younger and older drivers, using a systemic safety approach to develop risk factors and identify critical locations within the state. The study utilized crash, roadway, driver’s license, citation, healthy aging, and environmental justice data from various sources. Negative binomial regression models were developed to relate crash frequency with town-specific traffic, behavior, and site characteristics, considering exposure and spatial variance. The findings highlighted the significance of multiple risk factors contributing to severe crash frequency. For younger drivers, the presence of young drivers in the town, risk-taking behaviors such as unbelted and impaired driving, and infrastructure characteristics, particularly high-speed facilities and historically underinvested infrastructure, were key contributors to crash frequency. Older drivers’ crash frequency was influenced by the presence of older drivers, healthy aging indicators, risk-taking behaviors, and high-speed facilities. Based on the model results, risk scores were developed for each variable in the model and applied to each town. Towns were ranked using percentile ranking to classify them into primary and secondary risk categories. The towns identified in the primary risk category (18 towns in the top 5 percentiles) captured approximately 13.5% of severe younger driver crashes and 14.5% of severe older driver crashes.