City events are being organized more frequently, and with larger crowds, in urban areas. There is an increased need for novel methods and tools that can provide information on the sentiments of crowds as an input for crowd management. Previous work has explored sentiment analysis and a large number of methods have been proposed relating to various contexts. None of them, however, aimed at deriving the sentiments of crowds using social media in city events, and no existing event-based dataset is available for such studies. This paper investigates how social media can be used to estimate the sentiments of crowds in city events. First, some lexicon-based and machine learning-based methods were selected to perform sentiment analyses, then an event-based sentiment annotated dataset was constructed. The performance of the selected methods was trained and tested in an experiment using common and event-based datasets. Results show that the machine learning method LinearSVC achieves the lowest estimation error for sentiment analysis on social media in city events. The proposed event-based dataset is essential for training methods to reduce estimation error in such contexts.