Cerebrovascular abnormalities are critical indicators of stroke and neurodegenerative diseases like Alzheimer’s disease (AD). Understanding the normal evolution of brain vessels is essential for detecting early deviations and enabling timely interventions. Here, for the first time, we proposed a pipeline exploring the joint evolution of cortical volumes (CVs) and arterial volumes (AVs) in a large cohort of 2841 individuals. Using advanced deep learning for vessel segmentation, we built normative models of CVs and AVs across spatially hierarchical brain regions. We found that while AVs generally decline with age, distinct trends appear in regions like the circle of Willis. Comparing healthy individuals with those affected by AD or stroke, we identified significant reductions in both CVs and AVs, wherein patients with AD showing the most severe impact. Our findings reveal gender-specific effects and provide critical insights into how these conditions alter brain structure, potentially guiding future clinical assessments and interventions.