A computer learning, assessment and recommendation system to generate new information about the quality and degrees of walkability of sidewalks and walking routes through the collection, assessment and manipulation of large amounts of visual and geographic data, a scoring system, a rule-based computational methods and selected data representation are provided. Micro and macro data, methods and systems for sidewalk assessment generate various characteristics and qualities of routes creating general, locational and navigational functions using attributes and categories identified as important to walkability or to the experience of walking. Computed scores and recommendations displayed in maps and other visual tools and apps can be used by multiple client and sector groups including navigation, real estate, fitness, tourism and urban and rural development planning. This abstract complies with rules requiring abstract submission but does not limit the scope, interpretation or full meaning of the claims.