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Recent archaeological investigation of streets has revealed new insights on their role in the urban fabric of Roman cities (e.g., Hartnett 2017, Poehler 2017, Kaiser 2011, Laurence 2007). Intersections, however, which subdivide urban spaces into blocks, focus attention of passersby, provide a locus for public engagement, facilitate commerce, and more, have received only limited attention and their Latin vocabulary, remarkably, has not been examined. The ancient sources use three terms for intersections: compitum, quadrivium, and trivium. The etymologies of trivium and quadrivium, ‘three-ways’ and ‘four-ways’, indicate a more literal meaning, while compitum possesses a more figurative character, deriving from cum, ‘with’, and petere, ‘to ask, seek, trust or aim at’, yielding a meaning of “a rushing or coming together.” This paper will review key findings from analyzing nineteen Latin poets and prose authors, writing from the 1st century BCE to the 2nd century CE, comprising a corpus of over three and a half million words. The analysis reveals a significantly greater occurrence of trivium followed by compitum and quadrivium. A close review of the literary context demonstrates that trivium features in both a neutral/literal and negative context as in the gossipy and crowded cross-roads. Compitum, given its association with the Compitalia, appears regularly in a religious context but also in neutral/literal and negative contexts. The occurrences of quadrivium are too limited for definitive conclusions but it features solely in a negative context for the authors analyzed. Both trivium and compitum are employed widely across the profiled authors, thus, indicating no time-based preference; however, some authors, such as Horace and Juvenal, may exhibit a preference based on metrical qualities, while others, notably Vergil, do not. Further illuminating the textual analysis, material remains from Pompeii, Ostia, and Rome provide support for each intersection type with varying occurrences.