This talk and its subsequent workshop will introduce approaches to measuring syntactic properties in the English language, with a specific focus on large- and fine-grained syntactic measures. Approaches to measure syntax automatically through part-of-speech (POS) taggers and dependency parsers will be covered. The follow-up workshop will focus on how POS taggers and dependency parses can be used to assess language learner data at the large- and fine-grained levels in a large corpus focusing on English as a Second Language (EFL) learners. Data analysis techniques and hands-on data exploration will provide practical applications using learner corpora.