The world of 2050 will assuredly look different than that of 2012 in the fields of energy and transportation. The large deposits of easily accessible, conventional oil upon which the world has relied until now are in decline and will need to be supplemented with alternatives like electricity, hydrogen, biofuels, and non-conventional oils. The transition pathways are highly sensitive to economic, political, and environmental factors and are thus highly uncertain. Autopia is a simulation game designed to generate insights about the market dynamics of long-range fuel and vehicle transitions. Games have been shown to be valuable tools for generating robust, heuristic based approaches to problem domains that feature high degrees of uncertainty (i.e. uninsurable risk). Autopia simulates a three-way market of consumers, vehicle producers, and fuel producers. Human players take on player roles in the market and attempt to optimize their outcomes, relative to their competitors, within a given energy price and regulatory scenario. Analysis of game play has revealed several emergent patterns: 1) High fuel prices lead to a bifurcated vehicle market with small, cheap, gas powered vehicles dominating the low end of the market and high trim electrified vehicles (HEV, PHEV, BEV) dominating in the top 30% income bracket, 2) It is difficult to sell an alternative fuel vehicle that is easily comparable to a similar conventional vehicle due to the price difference, and 3) Aggregate gasoline demand in a mature market will fall given an improving average fuel economy, but predicting the decline will tend to cause fuel producers to under-produce. This research demonstrates a complete working prototype game, data analysis from actual games, and several insights into the system that I developed from observing multiple runs of the game