Some streets are better than others. Some are ordinary, and others are great. This paper explores what makes Great Streets and the key built form features. A case study analysis was conducted and was guided by an evaluative framework based on Allan Jacobs eight Requirements and five Criteria for Great Streets. The evaluative framework help assessed the degree to which Times Square and Yonge St - between Queen and College - met the Requirements and Criteria for Great Streets. The discussion demonstrates how improvement to the physical Requirements of streets can result in noticeable improvement in its’ function. While Yonge is Toronto’s ‘main street’ the evaluation identified areas for enhancement. Specifically, in order for Yonge to be a Great Street, future planning and design strategies should consider the following three Requirements: (1) Places to walk with some leisure; (2) Physical comfort; and (3) Quality Design.