We, herein, disclose a practical and straightforward alternative mechanochemistry‐driven strategy for the halogenation of a diverse series of bio‐relevant molecular scaffolds, such as 2‐(alkyl/aryl‐amino)naphthalene‐1,4‐diones, indoles, 1H‐ and 2H‐indazoles and coumarins, under additive‐ and reaction solvent‐free conditions. The salient features of the present method are additive‐ and solvent‐free synthesis, avoidance of using any external oxidants and heating, good to excellent yields, shorter reaction times in minutes, reusability of the solid surface, and gram‐scale synthetic applicability. In addition, we have extended the synthetic applications of the synthesized halo‐derivatives.