The city was initially founded between 1771 and 1776 but was soon after abandoned during the War of Independence. It was settled again shortly after the Restoration War in 1865.
Dajabón is located on the Dajabón River, also known as the Masacre River due to its connection to the Parsley Massacre of an estimated 20 to 30 thousand Haitians ordered by Trujillo in 1937. The river is shallow enough to make crossing on foot prevalent. The bridge across the river connects Dajabón to its larger Haitian sister city of Ouanaminthe. On Mondays and Fridays, Haitians are permitted to temporarily cross the bridge to sell their goods which mainly consist of the supplies donated to them by various organizations. Most of the goods are used clothes, shoes, and house-wear. On these days, an area of 20 square blocks of the city becomes a crowded business place. In addition to the Haitians, Dominicans go to the market to sell their food (vegetables grown in their part of the country).