The World Health Organization estimates that half of the world’s population is currently living in cities and will continue to climb. Cities are often vilified in many stories as ‘concrete jungles, slums,’ or seem terrifying to many. Thomas Jefferson believed that the strength and future of America lay in its rural heritage, and that cities were anathema to this concept. Perhaps the truth is that they are a culmination and reflection of the best and worst in our society. Cities are by their very nature, split personalities. Wasteful and ecoconscious. Chaotic in appearance, but concerned about efficiency, economies of scale, and marshalling the resources required to house, feed, clothe, educate, and move masses of people back and forth from home to work, and play. Many cities are also unique in that people gravitate toward them as centers of cultures and learning. The theme of this collection of urban short stories and poems revolve around life in the city during four seasons. In the section outlined, ‘Spring,’ for example, I start with an ode to New York, a poem dedicated to the city and its vibrancy, celebrating the dawn of something new and fresh. In the ‘Fall,’ section, on the other hand, I make historical reference to events of September 11th, 2001, in the poem Big Brothers. In between, the thematic expression of urban life and its experiences during the different seasons is laid out, sometimes metaphorically, as in the poem, ‘Shadow of Wings,’ which represents summer travel and freedom from the routines of life, and at times literally, as is in the short story, ‘South Station,’ where the main scene is played out in the winter.