Methods enabling direct C‐H alkylation of heterocycles are of fundamental importance in the late‐stage modification of natural products, bioactive molecules, and medicinally relevant compounds. However, there is a scarcity of a general strategy for the direct C‐H alkylation of a variety of heterocycles using commercially available alkyl surrogates. We report an operationally simple palladium‐catalyzed direct C‐H alkylation of heterocycles using alkyl halides under the visible light irradiation with good scalability and functional group tolerance. Our studies suggest that the photoinduced alkylation proceeds through cascade of events comprising, site‐selective alkyl radical addition, base‐assisted deprotonation, and oxidation. A combination of experiments and computations was employed for the generalization of this strategy, which was successfully translated towards the modification of natural products and pharmaceuticals.