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Natural and thermally modified Pine, Ash, and Acacia woods were exposed in two different environments: urban and maritime/industrial. The weathering effects were evaluated during 24 months regarding color, chemical, and structural changes. In all wood species, thermal modification induced color, chemical, and structural changes. All woods became darker (Pine ΔL*: −32.01; Ash ΔL*: −36.83; Acacia ΔL*: −27.50), total extractives content increased (Pine: 19 %; Ash: 32 % and Acacia: 18 %), and the samples presented deformation and damaged cells. Total lignin was not significantly changed, although there were detected changes in lignin, namely the reduction of G-units in Pine (≈2 %) and reduction of S/G ratio in Acacia (≈0.04 %). Ash remained almost the same. After weathering, modified woods suffered fewer color changes, indicating that the thermal modification could improve the resistance to color change. Acacia wood, when exposed to maritime/industrial conditions, revealed a higher color change (ΔE: 35.7 at 24 months) when compared with urban conditions (ΔE: 23.5 at 24 months). Delignification, possibly caused by photodegradation, occurred in all wood samples, and the loss of extractive happened, perhaps caused by rain. Modified woods were slightly less resistant to weathering in maritime/industrial environments. Some structural damage, namely cracked cells, the appearance of molds, blue staining, and particle deposition, was observed. The thermal modification enables color stabilization but does not seem to improve the weathering resistance in all studied wood species. Exposure to the different environments did not lead to significant differences in the morphology and chemical composition of the three natural and modified wood species.