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Repeat photography offers distinctive insights into ecological change, with ground‐based oblique photographs often predating early aerial images by decades. However, the oblique angle of the photographs presents challenges for extracting and analyzing ecological information using traditional remote sensing approaches. Several innovative methods have been developed for analyzing repeat photographs, but none offer a comprehensive end‐to‐end workflow incorporating image classification and georeferencing to produce quantifiable landcover data. In this paper, we provide an overview of two new tools, an automated deep learning classifier and intuitive georeferencing tool, and describe how they are used to derive landcover data from 19 images associated with the Mountain Legacy Project, a research team that works with the world's largest collection of systematic high‐resolution historic mountain photographs. We then combined these data to produce a contemporary landcover map for a study area in Jasper National Park, Canada. We assessed georeferencing accuracy by calculating the root‐mean‐square error and mean displacement for a subset of the images, which was 4.6 and 3.7 m, respectively. Overall classification accuracy of the landcover map produced from oblique images was 68%, which was comparable to landcover data produced from aerial imagery using a conventional classification method. The new workflow advances the use of repeat photographs for yielding quantitative landcover data. It has several advantages over existing methods including the ability to produce quick and consistent image classifications with little human input, and accurately georeference and combine these data to generate landcover maps for large areas. [ABSTRACT FROM AUTHOR]