A facile synthesis of tetrahydrobenzo[b]furans via gold(I)‐catalyzed cycloisomerization of 1‐aryl‐2‐propargylcyclohex‐2‐enols is described. The transformation is suggested to proceed through a gold(I)‐catalyzed tertiary allylic alcohol rearrangement to give a secondary allylic alcohol that underwent a 5‐exo‐dig addition of the hydroxyl group onto the gold(I)‐activated alkyne to give a vinylgold species. Protodeauration of the resulting vinylgold intermediate followed by aromatization furnished the tetrahydrobenzo[b]furans.