A general and efficient copper-catalyzed benzylation reaction of triazolopyridine with N-tosylhydrazones was developed. This reaction forms a C(sp²)–C(sp³) bond through cross-coupling, and represents an exceedingly practical method to afford 3-benzylated triazolopyridines in moderate to good yields. A proposed mechanistic pathway underlying this reaction was outlined. This catalytic transformation should enable broad synthetic applications in functionalization chemistry, allowing the synthesis of new pharmaceutically relevant triazolopyridine derivatives.