In Europe, mountain landscapes have evolved in a long‐term relationship with human communities and present‐day landscapes reflect that ancient interaction. The present study aims to reconstruct human activity in two mountain areas in northern Portugal using palynological analysis integrated with the available regional historical,archaeological and palaeoenvironmental archives. Pollen records from two sedimentary sequences span the Medieval and Modern periods and show that mixed agriculture and livestock grazing were consistently present in both regions throughout these times. Variations in cultural indicators show that the extent of farming fluctuated throughout time, with a general increase in cultivation during the Medieval period but with contractions likely coinciding with times of social disturbance. Historical sources suggest that socio political factors and population pressure were fundamental in the utilisation of upland spaces. This study did not find any convincing evidence to suggest that fire was a fundamental factor in heathland spread. We conclude that long‐term occupation of the uplands was sustained by low‐intensity land use throughout the Medieval to post‐Medieval periods, and that the present landscape has assumed a very different character following depopulation of the mountain areas and a shift towards commercial forestry.