Digital mapmaking has traditionally been a desktop computing activity with dedicated graphical (native or web) applications that strongly depend on the precision of mouse input. In addition, digital mapmaking also has a strong pillar on field observations, which have remained a separate task to the final mapmaking. In this work, we present to users a mobile application that combines the strengths of graphical mapmaking user interfaces with the actual geographical context into an integrated and collaborative user interface. In particular, the application implements three representative mobile mapmaking tasks (path recording, path editing and path reviewing) and includes gamification elements. A field experiment was conducted with thirty-six participants for two twenty-day periods during which they were asked to provide information about the pedestrian network of an urban region using the app. The results from questionnaire responses and contribution data showed that most users prefer recording their path, which is also the work with the lowest interaction. Moreover, gamification did not bring the expected results and the more difficult tasks were undertaken by few devoted users. Further research is needed to examine how interface design could better engage committed users in the aforementioned mapmaking task types.