The ubiquitous sameness of urban greenways prompts questions on generative design grammar and syntax, whether creative, critical rethinking at that level might be lacking. However the design syntax of urban greenways is not explicitly discussed thus leaving a critical gap in knowledge. This paper begins tackling the larger question by acting on the fundamental subset of it, by operationalizing the design syntax of urban greenways. This is done through mathematics-based graph studies to analyze patterns and shapes, photography based thermal, material and morphology studies, and section analyses to make imagery-derived deductions on the design syntax. Recommendation on approaches to diversify and enrich the design syntax includes a more direct reference from ecosystem science theories such for siting and planning the urban greenways at macro- to meso-scale, a mixed-method approach, combining mathematics, photography and drawings based frames for analyses at meso-, to micro-scale, and a turtle view scale for designing at meso- to micro-scale, with an emphasis on latter.