Long term (from the Mesolithic to the Bronze Age) habitation of the Akali settlement on a clearly defined bog-island in East Estonia is used as an example of transitional development from a prosperous foragers’ habitation centre to a hinterland of established farming cultures, taking place through availability, substitution and consolidation phases of crop farming in the boreal forest zone. The pre-Neolithic finds of Triticum and Cannabis t. pollen at c. 5600 b.c. are interpreted as possible indications of the acquaintance of foragers with farming products, through contacts with central European agrarian tribes during the availability phase. The substitution phase is marked by more or less scattered pollen finds of various cereals and hemp and, at Akali, is connected with Neolithic period 4900–1800 b.c. An increasing importance of crop farming in the economy is characteristic of the consolidation phase, but because natural conditions are unfavourable for arable land-use, a regression of human presence is recorded during the second part of the Neolithic. The settlement was abandoned during the Bronze Age at the time when crop farming become the basis of the economy in Estonia. The re-colonisation of the area, traced to ca. a.d. 1200, took place for political reasons rather than through increasing suitability of the landscape.