Abstract Treatment of 3‐(or‐hydroxybenzyl)pyrazolo[1,5‐a]pyridines with trifluoroacetic acid in dichloromethane resulted in the formation of pyrazolo[1,5‐a]pyridines, bis[α‐(pyrazolo[1,5‐a]pyrid‐3‐yl)benzyl] ethers, and phenylbis(pyrazolo[1,5‐a]pyrid‐3‐yl)methanes, depending upon the presence or absence of the substituents at the 2‐ and/or 4‐positions and the reaction conditions employed.