Abstract. Mapping woody cover over large areas can only be effectively achieved using remote sensing data and techniques. The longest continuously operating Earth-observation program, the Landsat series, is now freely-available as an atmospherically corrected, cloud masked surface reflectance product. The availability and length of the Landsat archive is thus an unparalleled Earth-observation resource, particularly for long-term change detection and monitoring. Here, we map and monitor woody vegetation cover in the Northwest Province of South Africa, an area of more than 100,000 km2 covered by 11 Landsat scenes. We employ a multi-temporal approach with dry-season data from 7 epochs between 1990 to 2015. We use 0.5 m-pixel colour aerial photography to collect > 15,000 point samples for training and validating Random Forest classifications of (i) woody vegetation cover, (ii) other vegetation types (including grasses and agricultural land), and (iii) non-vegetated areas (i.e. urban areas and bare land). Overall accuracies for all years are around 80 % and overall kappa between 0.45 and 0.66. Woody vegetation covers a quarter of the Province and is the most accurately mapped class (balanced accuracies between 0.74-0.84 for the 7 epochs). There is a steady increase in woody vegetation cover over the 25-year-long period of study in the expense of the other vegetation types. We identify potential woody vegetation encroachment 'hot-spots' where mitigation measures might be required and thus provide a management tool for the prioritisation of such measures in degraded and food-insecure areas.