© 2014 IEEE.This paper demonstrates a framework for a digital heritage research, Augmenting Kashgar, that facilitates the revitalizing of a historical architecture by using gamification, shape grammars and virtual reality. Examining current use of new media technologies, our methodology initially merges shape grammars, a generative modelling method, with gamification. It then extends the use of game elements into virtual reality in which the synthesizing of the old culture with a new one is the main accomplishment being sought. Firstly, gamification maps a community engagement plan while shape grammars serve for spatial analysis of the narrow alleys of Kashgar. Secondly, the gamified platform transitions from screen-based experience to immersive virtual reality interpretations.