Semiotics is debatable as a philosophy for architecture today but it is a useful tool in design and decoding what already exists. Augmented Reality is an emerging field where massive and rapid growth is taking place today. Weaving semiotics, augmented reality , gaming and architecture into one beautiful mesh we get a solution for urban regeneration in the city of Lincoln, UK, a small city known for its Cathedral and its University. How will semiotics provide a philosophical pathway for taking forward urban regeneration of places in the city which have been left under utilized? This material was submitted as part of an examination while the author undertook the study in Semiotics of Architecture in Lincoln University ,UK in the years 2008-09, supervised by Dr. Kathleen Watt. Exploring different seemingly unrelated fields led to the culmination of one whole year of study answering the questions how and why?