An efficient route to pyrazolo[1,5-a]pyridines by Cu(OAc)₂-promoted oxidative [3 + 2]-annulation of nitroalkenes with in situ generated pyridinium imines is developed. The reaction with α-fluoronitroalkenes enables the first preparative synthesis of 3-fluoro-pyrazolo[1,5-a]pyridines. Cycloaddition with α-unsubstituted nitroalkenes provides access to 3-nitro-pyrazolo[1,5-a]pyridines in excellent yields. A broad transformation scope was demonstrated. Both electron-rich and electron-deficient nitroalkenes as well as different aminopyridinium salts can be used for the assembly of the target pyrazolo[1,5-a]pyridines. The related aza-heterocycles, namely, pyrazolo[1,5-a]pyrazines and pyrazolo[1,5-b]pyridazines, were successfully prepared via the present methodology. The possible mechanism of the reaction is discussed.