This study answers the following research questions: 1) What are the change trajectories of woody vegetation elements at the landscape level? 2) What are the differences in change trajectories amongst the various categories of forest, non-forest and reclamation woody vegetation? 3) How do the change trajectories differ in mining and non-mining landscapes? The study area, measuring 209.6 km2, is located in the north-western part of the Czech Republic and may be broken down into 76.8 km2 of mining landscape and 132.8 km2 of non-mining landscape. Brown coal mining began in this region during the second half of the 18th century and led to the radical transformation of the landscape, including woodlands, during the second half of the 20th century. The source data for this study was obtained from the original stable cadastre maps (1842) and the landscape field mapping performed in 2010. The various woody vegetation elements (forest, non-forest, and reclamation woody plants) and land use/cover (LULC) categories were identified. The GIS symmetrical difference tool was subsequently used to perform an overlay analysis for the individual woody vegetation elements in order to study the change trajectories and to obtain information about the woodlands that have remained unchanged (continuous), the ones that have disappeared (extinct), and the ones that have newly appeared in the landscape (recent). In the case of the non-mining landscape, the total proportion of woodlands has increased (from 17 to 32%), but there has been a decline in the overall volume of forest woody plants found in these areas (from 93 to 74%). As far as the mining landscape is concerned, there has also been an increase in the area covered by woodlands (from 10 to 20%), however, the proportion of forest woody plants has decreased to a much greater extent (from 90 to 31%). From the perspective of extinct woody vegetation, 23.3% of all types of woodlands in the mining landscape may be classified as such, as compared to 10.8% in the non-mining landscape. The primary causes of this decline are mining activities and newly built-up areas. More continuous woody vegetation may be found in the non-mining landscape (42.1%) as compared to the mining landscape (15.4%). Recent woody vegetation, which has primarily replaced grasslands and partially arable land, prevails in both the mining (61.3%) as well as the non-mining (47.1%) landscapes. Different categories of woodlands (forest, non-forest, and reclamation woody vegetation elements) exhibit various change dynamics due to their different structure and the functions they serve. At the most basic level, there has been an overall increase in the occurrence of woodlands in the studied areas. However, once GIS spatial analysis is applied it is possible to see more complex processes in the development of woodland areas as characterised by gains and losses, and it is possible to identify mining and agricultural extensification as the two most significant factors behind the historical changes. Mining leads to a direct decrease in the area of woodlands; conversely, the spontaneous succession of vegetation resulting from agricultural extensification and forest reclamation facilitates woodland recovery. Forest reclamation and reforestation are essential on order to ensure the time continuity of woodlands in both types of landscape, i.e. mining and non-mining. The study presented in this paper proves that it is relevant to analyse the changes occurring in different woodland categories separately. The same methodology may be applied when studying the change dynamics of other important landscape elements, such as wood pastures and wetlands.