A novel series of 1,2,3-triazole-genipin analogues were designed, synthesized, and evaluated for neuroprotective activity, acetylcholinesterase (AChE), and butyrylcholinesterase (BuChE) inhibitory activity. The genipin analogues bearing bromoethyl- and diphenylhydroxy-triazole showed in vitro neuroprotective properties against H2O2 toxicity along with potent inhibitory activity on BuChE with IC50 values of 31.77 and 54.33 μM, respectively, compared with galantamine (IC50 = 34.05 μM). The molecular docking studies of these genipin analogues showed good binding energy and interact well with the key amino acids of BuChE via hydrogen-bonding and hydrophobic interactions. Triazole genipins might be promising lead compounds as anti-Alzheimer’s agents.