A new synthesis of 4-halo-1H-indoles has been developed from easily available 2,3-dihalophenol derivatives. The key steps are Smiles rearrangement and a one-pot or stepwise Sonogashira coupling/NaOH-mediated cyclization. Subsequent functionalization allows access to a wide variety of 2,4- or 2,3,4-regioselectively functionalized indoles.