Headache is a milestone in cerebrovascular disorders; indeed, it may represent the only symptom at onset or predominates over the other neurological features. Unfortunately, headache associated with cerebrovascular diseases lacks clear-cut characteristics as it may resemble a migraine attack, tension-type headache, or cluster headache; pain localization is also misleading along with drug (analgesic) response. However, in this review, we have analyzed and described the most common patterns of headache for different vascular disorders: it is known that headache due to subarachnoid aneurysmal hemorrhage presents peculiar characteristics (thunderclap, acute presentation, and high intensity), whereas in cerebral vasoconstriction syndrome, the short duration and the relapsing-remitting course of the thunderclap headache are key points for the diagnosis; in cervicocerebral artery, dissection pain is most commonly ipsilateral to the dissected vessel and is mainly perceived in the temporal area in case of carotid artery dissection and in the occipital area in case of vertebral artery dissection; in cerebral venous thrombosis, pain is often acute or subacute and severe; unfortunately, it may resemble a typical migraine attack or a tension-type episode; by the contrary, in primary angiitis of the central nervous system, pain is always subacute or chronic with mild-to-moderate intensity; finally, in brain arteriovenous shunts such as malformation or fistula, pain is more frequently a clue for disease complication such as hemorrhage from the malformation or thrombosis of the draining vein.