Dry-stone masonry retaining walls are vulnerable to bulging and leaning because of the lack of cohesion between stones. Currently, the structural integrity of these walls is mainly assessed by qualitative judgments informed by visual inspections. Photogrammetry has the potential to increase the quality and objectivity of retaining wall inspections. This technology uses a series of images to generate a detailed 3D model of a structure. Currently, this technology is most commonly used in civil engineering applications for mapping large areas, often using aerial photographs. In this study, photogrammetry is used in two field trials to evaluate its ability to create accurate, high-resolution 3D representations of masonry retaining walls in Connecticut. The 3D models were used to document the current in-situ conditions to provide a baseline for future comparisons, as well as show cross sections of vulnerable areas, such as bulges or tilts. In one trial, data were collected on two dates to show the progression of movement of the wall. This paper gives an overview of best practices for data collection and discusses results and observations from the field trials. The generated 3D models provide an enhanced form of inspection documentation including detailed representations of geometry and colors. The contribution of this paper is to provide material facilitating the adoption of this promising technology for the inspection of masonry retaining walls and other transportation infrastructure.