The assessment of behavioral traits in dogs is a well-studied challenge due to its many practical applications such as selection for breeding, prediction of working aptitude, chances of being adopted, etc. Most methods for assessing behavioral traits are questionnaire or observation-based, which require a significant amount of time, effort and expertise. In addition, these methods are also susceptible to subjectivity and bias, making them less reliable. In this study, we proposed an automated computational approach that may provide a more objective, robust and resource-efficient alternative to current solutions. Using part of a Stranger Test protocol, we tested n=53 dogs for their response to the presence and benign actions of a stranger. Dog coping styles were scored by three experts. Moreover, data were collected from their handlers using the Canine Behavioral Assessment and Research Questionnaire (C-BARQ). An unsupervised clustering of the dogs' trajectories revealed two main clusters showing a significant difference in the stranger-directed fear C-BARQ factor, as well as a good separation between (sufficiently) relaxed dogs and dogs with excessive behaviors towards strangers based on expert scoring. Based on the clustering, we obtained a machine learning classifier for expert scoring of coping styles towards strangers, which reached an accuracy of 78%. We also obtained a regression model predicting C-BARQ factor scores with varying performance, the best being Owner-Directed Aggression (with a mean average error of 0.108) and Excitability (with a mean square error of 0.032). This case study demonstrates a novel paradigm of digitally enhanced canine behavioral testing.