Social media reviews and Natural Language Processing (NLP) techniques enable the exploration of users' on-site emotions in urban landscapes. These technologies have supplemented, and in some cases replaced, many traditional data collection and analysis methods for understanding people’s sentiments about places. However, existing literature lacks studies using these approaches within landscape and urban design research. Using a case study from North America, we examine the usefulness of VADER, a sentiment analysis tool, to understand users' emotions towards different urban landscapes. Results showed that seasonal changes did not significantly impact users' emotions towards different urban landscapes, but some urban functions elicited higher positive emotions during the study period. This investigation demonstrates the usefulness of VADER for evaluating people's sentiments towards urban landscapes.