In this analysis, we will be analyzing a collection of texts that are tagged with a grade level to determine the best factors for measuring readability. Readability is typically represented using a decimal: the integer part is the corresponding “grade level” from pre-Kindergarten to professional and the decimal part represents a month of that grade level in which the average individual in that grade level would be able to comprehend the passage. Classical methods use word length and sentence length as a proxy for readability. Our analysis will focus on determining which characteristics of a passage best predict the readability of the passage and developing a model that will use these characteristics to predict the readability level of a passage. These characteristics include word frequency, transitions between sentences within a paragraph as well as the model of paragraph transitions within the passage.