Providing students with opportunities to build, and test and revise ideas, can help them develop critical thinking and problem-solving skills. In this article, the authors describe how core measurement and geometry concepts were embedded within a "Model It!" task. They replicate an industry-based, interdisciplinary problem, but only focus on the mathematical ideas here. Twenty-six Algebra 1 students worked on organizing gingerbread houses within a community and designing the path and operation of a mini-trolley tour. Starting work on these tasks required that students keep the task specifications in mind. With guidance from their teacher, the students sub-divided their modeling work into creating three designs: (1) trolley path design, (2) gingerbread community design, and (3) a two-dimensional (2D) model of the gingerbread community to fit the resort ballroom.