Measures of vegetation structure are often key within ecological restoration monitoring programs because a change in structure is rapidly identifiable, measurements are straightforward, and structure is often a good surrogate for species composition. This paper investigates the use of drone-based digital aerial photogrammetry (DAP) for the characterization of the structure of regenerating vegetation as well as the ability to inform restoration programs through spatial arrangement assessment. We used cluster analysis on five DAP-derived metrics to classify vegetation structure into seven classes across three sites of ongoing restoration since linear disturbances in 2005, 2009, and 2014 in temperate and boreal coniferous forests in Alberta, Canada. The spatial arrangement of structure classes was assessed using land cover maps, mean patch size, and measures of local spatial association. We observed DAP heights of short-stature vegetation were consistently underestimated, but strong correlations (rs > 0.75) with field height were found for juvenile trees, shrubs, and perennials. Metrics of height and canopy complexity allowed for the extraction of relatively tall and complex vegetation structures, whereas canopy cover and height variability metrics enabled the classification of the shortest vegetation structures. We found that the boreal site disturbed in 2009 had the highest cover of classes associated with complex vegetation structures. This included early regenerative (22%) and taller (13.2%) wood-like structures as well as structures representative of tall graminoid and perennial vegetation (15.3%), which also showed the highest patchiness. The developed tools provide large-scale maps of the structure, enabling the identification and assessment of vegetational patterns, which is challenging based on traditional field sampling that requires pre-defined location-based hypotheses. The approach can serve as a basis for the evaluation of specialized restoration objectives as well as objectives tailored towards processes of ecological succession, and support prioritization of future inspections and mitigation measures.