This article concentrates on the author’s efforts to produce the first translation of Mark Twain’s 1884 novel Adventures of Huckleberry Finn into colloquial Arabic, and briefly reviews a few other major translations of Twain’s masterpiece into Modern Standard Arabic and Classical Arabic. The article reflects on this ongoing translation project attempting to present Twain’s book in a vernacular Arabic dialect spoken in Damascus and the countryside surrounding the Syrian capital. It highlights and explains the rationale and inspiration behind this unique translation project as well as the reasons behind the selection and employment of this specific regional Damascene dialect. The article also discusses and exemplifies how all previous Arabic translations of Twain’s novel used Modern Standard Arabic and Classical Arabic and were affected by a motley assortment of cultural, political and religious factors that resulted in abridgement, adaptation, and censorship. These previous translations partially failed to capture the freshness of Huck Finn’s casual voice, childish tone, and cluttered storytelling, along with the perceptiveness and seriousness of Twain’s authorial intention, themes and comedy.