The Cognitive Expertise through Repetition-Enhanced Simulation (CERES) project is aimed to provide a novel approach to accelerating the development of expertise in topographic map reading skill. Practice at this complex cognitive skill is accomplished through rapid-paced, simulation-based training events with a large procedurally generated database of training content items to provide continuing novel challenges. On each short training event, participants are presented with simultaneous views of a novel topographic map and a video render of first-person perspective movement through the terrain. The trainee goal is to identify what position on the map is reflected by the movement clip. Trainee performance level was continually assessed during training and the difficulty of training content was adjusted adaptively to enhance learning and maintain engagement and motivation with the training task. Data are reported from a sample of naïve online participants (n = 37, 169 h of total training) who acquired topographic map reading skill based on their experience with the CERES protocol. Participants without any prior topographic map reading training or experience nevertheless exhibited improved performance over training. In addition, a substantial subgroup also demonstrated very high levels of engagement and motivation with the training protocol. We conclude that the approach of rapid-paced training to induce practice with a complex cognitive skill can be administered in an individualized adaptive manner to accelerate the development of skilled expertise.