Context driven environments are growing in popularity. Mobile applications, Internet of Things devices, autonomous vehicles, and future technologies respond to context events in their environments. This work uses a set of context events from real users to guide the generation of context driven test cases. Context event sequences are obtained by applying Conditional Random Fields (CRF). Test suites are then constructed by interleaving the context event sequences with GUI events. The choice of context event is made based on transitions obtained from the CRF. Results of the empirical studies show that techniques that incorporate context events provide better code coverage than NoContext for the subject applications. A heuristic technique introduced in this work, ISFreqOne, yields 4x better coverage than NoContext, 0.06x better coverage than Random Start Context, 0.05x better coverage than Iterative Start Context, which are control context generation techniques, and 0.04x better coverage than ISFreqTwo, another heuristic introduced in this work.