This fertile region of lush high-mountain valleys and rushing rivers was the most populous of all the Taíno regions in what is today the Dominican Republic when the Spaniards arrived in 1492.
Just north of the modern city of San Juan de la Maguana is the ancient Corral de los Indios, a vast plaza where the famous Cacica Anacaona once hosted fabulous “areitos,” community-wide song and dance celebrations. It was an isolated region for centuries, where Indians and African slaves ran to in order to escape their Spanish overlords. In that time, its multi-ethnic peoples developed many colorful dances, festivals, and magico-religious beliefs and rituals (including what is commonly called “voodoo”) that make the region one of the most colorful in the nation for its folkloric manifestations. It is also home to Papá Liborio altars (Liborio was an early 20th-century religious leader who still has fanatical followers), a monument to the Battle of Santomé, has two beautiful recreational areas formed by the dams at Sabaneta and Sabana Yegua, and shares the national park of José del Carmen Ramírez with its neighboring province of Azua.
San Juan de la Maguana is one of the oldest cities in the country. It occupies the same valley as that of the old Maguana cacicazgo and the historic Indian Corral.
San Juan de la Maguana was originally founded in the beginning of the 16th century, around 1504, at the shores of the San Juan River, near the section now known as Manoguayabo, by Captain Diego Velázquez, who was carrying out an order of Nicolás de Ovando.
From its very beginning San Juan was a flourishing villa due to the rich soil and smooth weather. The sugar cane industry was its settlers main occupation. It possessed four sugar mills during its early beginnings. The first of these mills was installed in the center of the town. San Juan de la Maguana was a municipality of the Azua province until 1939.
Some important historical events that took place in San Juan de la Maguana include: The black slave revolt, known as the "cimarronada", that began in Haina had repercussions throughout the San Juan province since black leader Sebastián Lemba (1513 - 1548), used the section of Sosa as a hideout.
Cacique Enriquillo lived in the region known as La Higuera and it was from there that he began what is known as the Enriquillo Rebellion, which culminated in the Enriquillo Peace treaty in 1533. Enriquillo was the first warrior to apply guerilla tactics in America.
The Battle of Santomé, fought on December 22, 1855 between Haitians and Dominicans, resulted in a victory for the Dominican army led by General José María Cabral; this encounter sealed the country's National Independence. The patron saint festivities are celebrated on June 24 each year in honor of San Juan Bautista.