This paper, co-written by Haozhuo Yang, a recipient of Perkins Eastman’s 2023 Design and Wellness Fellowship, introduces a novel approach using Visual AI to assess urban walkability for older adults, offering a more precise, human-centered alternative to traditional GIS-based methods. By leveraging Google Street View images and Hong Kong’s Travel Characteristics Survey, the research quantifies the impact of urban features—such as benches, trees, sidewalks, and crosswalks—on walking behavior. Findings reveal that well-designed streetscapes with seating, greenery, and connected pathways significantly enhance mobility and social engagement. The study also establishes data-driven design guidelines, providing urban planners with a scalable AI-powered tool to create more inclusive, pedestrian-friendly environments that support aging populations.