Recent experimental studies have shown that anthocyanins (ACNs) can be used as effective acetylcholinesterase (AChE) inhibitors to prevent Alzheimer's disease (AD), but the relationship between the type of ACNs and AChE inhibition ability remains unclear. The inhibitory ability of eight kinds of ACNs-rich foods (blueberry, mulberry, black rice, purple corn, purple potato, purple cabbage, kale and rose) on AChE was evaluated in our study. A total of 93 ACNs monomers were detected by UPLC-MS/MS. In vitro inhibition assays demonstrated that all eight crude ACNs extracts exhibited inhibitory activity against AChE, with IC50 values ranging from 32.6 to 312.2 μg/mL. Among these, blueberry ACNs showed the strongest inhibitory capacity. The combined analysis of ultraviolet spectrum, fluorescence spectrum, circular dichroism spectrum and fourier transform infrared spectrum shows that static quenching plays a dominant role in the binding process, and there is no significant conformational change in AChE. Molecular docking proved that the binding energy of Malvidin-3-O-galactoside in blueberry was the highest, which was −8.86 kcal/mol. This study aims to provide more choices and more scientific guidance for individuals to select ACNs in daily diet to prevent AD.