A tension-type headache (TTH) is a recurrent headache that is mild to moderate in intensity, unlike migraine (MH), which is accompanied by crippling effects of nausea, vomiting, photophobia, or phonophobia. TTH is more frequent than migraine, but it is less likely to cause severe pain and physical dysfunction. TTHs account for more lost workdays due to their prevalence. The study aimed to evaluate the prevalence, frequency, and disability of MHs and TTHs among the general population in the Eastern Region of Saudi Arabia. A cross-sectional study was employed using a validated questionnaire. The questionnaire implemented the HARDSHIP algorithm to diagnose MH and TTH and questions to correlate their prevalence to socio-demographic data, measurement of the level of disability, headache management, and treatment effectiveness using the chi-square test. The study reviewed 877 subjects (46.6% males vs. 53.4% females). 52.9% of the participants experienced headaches during the previous three months, and 35.6% experienced headaches recently. The most common type of headache was a probable MH (32.1%), followed by a TTH (26.9%), probable TTH (19.5%), and MH (15%). It was reported that some disability was attributed to 47% of MHs and 26% of TTHs. The most commonly used headache medication was paracetamol (53.5%). This study revealed that TTH and MH are common illnesses in Saudi Arabia’s Eastern Region. TTH and MH are correlated with significant individual and social burdens, particularly for MH. Headache sufferers mostly manage their headaches using conventional over-the-counter methods.