Wood surface modification is a comprehensive concept which, in time, turned out to be as successful as challenging when it comes to improve the resistance of wood during its life cycle in both indoor and outdoor applications. The initial approaches have aimed at simple methods with immediate results. Nowadays, the paradigm has slightly changed due to the scientific and technical advances, and some methods has become intermediate stages in more complex processes, after being used, for long time, as stand-alone procedures. The esterification was employed as a convenient method for wood surface modification due to the high amount of free hydroxyl groups available at the surface of wood and other lignocellulosic materials. Therefore, different esterification approaches were tested: activated condensation with carboxylic acids (monocarboxylic, as well as dicarboxylic acids, fatty acids, etc.) in the presence of condensation activating agents (such as trifluoroacetic anhydride); reaction with β-halogen-substituted carboxylic acids; esterification using carboxylic acids derivatives (acyl chlorides, anhydrides) or even multifunctional carboxylic acids (i.e., tricine). Thus, wood with improved dimensional stability and weathering resilience, higher fire resistance, enhanced hydrophobic character, and mechanical durability was obtained. This paper offers an overview of some of the most recent advances reported in the field, presented in a systematic manner, using the type of reaction as classification criterion. The main improvements will be outlined in a critical assessment in order to provide an useful tool for a wise choice in future applications.