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In this paper, the features of the natural and geographical conditions of the northern forest-steppe of the Middle Irtysh region, which Russian peasants began to develop at the beginning of the 18th century, are examined. The criteria that led the peasants to consider these lands convenient for resettlement have been analyzed. Nowadays, these lands belong to the Gorkovsky and Sargatsky districts of the Omsk Region. The sources for conducting this work were represented by archaeological, ethnographic, and geographical data on this area. The author believes that the natural conditions of the right and left banks differ significantly in the studied area. On the left bank, there is a wide floodplain with a large number of the flooded lakes, small rivers and streams. On the floodplain, there are uplands which become islands during the floods. On the left bank, two lines of villages appeared: the first was located on the terrace of the Irtysh River, the second — along the hills on the floodplain. The terrace approaches closely the right bank of the Irtysh; therefore, the cases of coastal collapse and the associated processes of intensive formation of the ravines are frequent there. There is a small amount of water of good quality, while the groundwater runs at a depth of more than 20 m; therefore, cascades of dams were built in the ravines. The villages are arranged in two lines, first of which is located directly on the terrace, most often at the mouths of the ravines. The second line of the villages is 8–12 km from the terrace at the tops of the ravines. Here, good quality groundwater is available at a depth of about 3 m. Arable lands, comprising rich black soil, stretch along both banks of the Irtysh. With distance from the Irtysh, more and more lands appear to be less suitable for agriculture. Therefore, these areas were populated later than the banks of the Irtysh. Landslide processes, stimulating the active formation of the ravines on the right bank of the Irtysh, were unfavorable in a long term perspective. Firstly, they occurred with a period of 50 years. Secondly, the coast collapsed at its maximum over about 1 km length. Therefore, the first settlers might have not known about these processes. However, if one takes into account the patterns of the resettlement of the indigenous population, then the absence of archaeological sites does not necessarily indicate uninhabitedness of the territory, since their settlements could have been destroyed. Although in general, if one to talk about the criteria of the favorableness of land for resettlement, then the presence of not only land, but also arable land and good water must be contemplated.