This study assessed whether methods for capturing the pedestrian experience of outdoor lighting, previously evaluated in a full-scale laboratory, were applicable in a real-world setting. It applied an approach capturing the human response to outdoor lighting in a systematic way, by assessing perception, evaluation and behaviour in the lit environment. The study involved 81 participants from two age groups (Young—n: 48, mean age: 26, 63% women; Elderly—n: 33, mean age: 69, 67% women) and was carried out on a pedestrian path in a park in the centre of Malmö, Sweden, in the evenings during wintertime. Two LED lighting applications, differing in light distribution, uniformity and horizontal illuminance, were presented, and the pedestrians’ perception (facial expression recognition and sign reading), evaluation (arousal, valence and perceived outdoor lighting quality) and behaviour (pedestrian flow) were assessed. The results from the perceptual tasks differed significantly between the lighting applications, in favour of the lighting application with greatest uniformity and horizontal illuminance. There was a significant difference in sign reading distance between the two age groups. The methods applied in this study are feasible to administer and could be used to assess lighting solutions in order to capture the needs of vulnerable groups.