The Spanish conquistador Francisco Hernández de Córdoba personally founded the city of Segovia on the banks of the Río Coco where it met the Jícaro, and the first settlers began exploring for veins of gold in the nearby hillsides.

But the Spanish abandoned this early settlement and moved farther north along the Río Coco. The Xicaque, Miskito, and Zambo tribes attacked the new settlement with growing ferocity, however, strengthened and emboldened by shiny new firearms from the British, and English pirate Henry Morgan later sailed up the Río Coco and reduced the city to rubble.

The Spanish moved west to the present village of Ciudad Antigua, which became the Segovian capital despite continued attacks. Not until the early 19th century did the little village of Ocotal begin to assume any importance, when the Catholics transferred valuable religious artifacts to the new church of Nuestra Señora de la Asunción. The faithful followed the relics westward, and Ocotal began to grow.

In the early 1930s, General Sandino and his men were firmly entrenched in the mountains north of Ocotal, and the American government, intent on capturing him, sent in the Marines. Based in Ocotal, they scoured the countryside around Cerro Guambuco and built the country’s first airstrip in Somoto, from which they launched strikes on the city of Ocotal, the first city in the history of the world to experience an air raid.

During the 1980s, much of the conflict between Sandinistas and Contras took place in the same area, fiercely punishing outpost towns like Jalapa.