Unlike car navigation, where almost all vehicles can traverse every route, one route might not be optimal or even suitable for all pedestrians. Route geometry information, including tortuosity, twists and turns along roads, junctions, and road slopes, among others, matters a great deal for specific types of pedestrians, particularly those with limited mobility, such as wheelchair users and older adults. Offering practical routing services to these users requires that pedestrian navigation systems provide further information on route geometry. Therefore, this article proposes a novel method for extracting and analyzing the geometry properties of the shortest pedestrian paths, with a focus on open geospatial data across four aspects: (a) similarity, (b) route curviness, (c) road turns and intersections, and (d) road gradients. Deriving from the Hausdorff distance, a metric called the “dissimilarity ratio” was developed, allowing us to determine whether pairs of routes show any tendencies to be similar to each other. Using the “sinuosity index”, a segment-based technique quantified the route curviness based on the number and degree of the road turns along the route. Moreover, relying upon open elevation data, the road gradients were extracted to identify routes offering smoother motion and better accessibility. Lastly, the road turns and intersections were investigated as pedestrian convenience and safety indicators. A local government area of Greater Sydney in Australia was chosen as the case study. The analysis was implemented on OpenStreetMap (OSM) shortest pedestrian paths against Google Maps as a benchmark for real-world commercial applications. The similarity analysis indicated that over 90% of OSM routes were identical or roughly similar to Google Maps. In addition, while Spearman’s rank correlation showed a direct relationship between route curviness and route length, rS(758) = 0.92, p < 0.001, OSM, on average, witnessed more tortuous routes and, consequently, shorter straight roads between turns. However, OSM routes could be more suitable for pedestrians when the frequency of intersections and road slopes are at the center of attention. Finally, the devised metrics in this study, including the dissimilarity ratio and sinuosity index, showed their practicability in translating raw values into meaningful indicators.