This paper presents the results of a pilot field study of the Russian language of a group of East Siberian old settlers in the context of their ethnic and cultural history and their role in Russian expansion eastward, including Alaska between the eighteenth and nineteenth centuries. From a linguistic perspective, the regional features of the old settlers’ Russian language testify to the cultural and historical processes that involved various groups of the Russianspeaking population of Eastern Siberia. This paper aims at comparing these linguistic materials to the data on the Russian language of Alaska found by the authors, which may help clarify the historical processes that shaped the Russian linguistic and cultural landscape of Alaska, the only overseas Russian region. Linguistic data from Siberia are checked against those of Alaskan Russian – a language of intercultural communication in Alaska from the beginning of the Russian America period (mid-eighteenth century) and through to the mid-twentieth century. The research on Alaskan Russian is based on the variant spoken in Ninilchik (Kenai Peninsula) that has survived until the present time. The lexical, grammatical, and phonological features of Ninilchik Russian demonstrate both contact features of this idiom and its peculiarities as a variant of Russian. This description is followed by data from the language of the so-called “teamster old settlers” from the Pokrovsk region in Yakutia. It is known that Russian old settlers from Siberia, and especially teamster old settlers, made up a considerable part among the Siberian Russians who were coming to Alaska in the nineteenth century. However, drawing on a comparison of the two sets of linguistic data, the authors conclude that the dialect they speak is quite different from the varieties of Russian spoken in Alaska.