After the durability of wood against wood decay fungi, its water performance is the next most important factor that influences the performance of wood in outdoor, above-ground applications. It is therefore of major importance to optimize methods that are able to predict the moisture behaviour of wood in outdoor applications. In order to elucidate these questions, samples were prepared from European oak (Quercus robur/Q. petraea), sweet chestnut (Castanea sativa), European larch (Larix decidua), Scots pine heartwood and sapwood (Pinus sylvestris), Norway spruce (Picea abies) and beech (Fagus sylvatica). The moisture performance of the samples was altered by thermal modification, wax, oil and biocide treatment. Two types of specimens were prepared; smaller specimens (1.5 × 2.5 × 5.0 cm) were exposed to natural weathering for three periods (9, 18 and 27 months) and subsequently analyzed in the laboratory with various methods (contact angle, short- and long-term water uptake and water vapor uptake). In parallel, bigger specimens (2.5 × 5.0 × 50 cm) were exposed outdoors in a monolayer exposure and equipped with moisture monitoring sensors for 18 months. Water performance of wood could change as a result of weathering, being the most evident at thermally modified wood, where the decrease of the moisture performance was the most evident. The results of the study clearly showed that the water performance of the majority of the materials decreased with natural weathering. These results indicate that in order to elucidate the moisture performance of wood fully, a variety of laboratory tests needs to be applied, relating to both liquid water performance and water vapour interactions with wood.