This research dwells upon prominent Russian writer Alexander Pushkin’s poetry in light of translation. More specifically, one of Pushkin’s most famous poems – “Winter Evening” – has been selected to be analyzed with regard to its translation in Armenian and English. This study aims to reveal the major challenges that the translators have faced while rendering the poem from Russian into Armenian and English as well as to disclose the discrepancies that exist between the original and the translated texts. Also, an attempt will be made to identify the major lexical, grammatical, stylistic and syntactic shifts that have occurred in the translation process in order to assess the degree of translation accuracy and pinpoint whether or not the translated texts impact the target-language readers to the same extent as the original.