When in 1536 Gonzalo Jiménez de Quesada organised the main expedition into the Colombian Andes, he named De Céspedes as one of eight captains; of cavalry. At this expedition also his brother Hernando de Prado joined. In the lower parts of the Magdalena River, at the confluence with the San Jorge and Cauca Rivers, Juan de Céspedes and Juan de Sanct Martín reached first and were joined by the other troops of De Quesada. After the journey of a year into the Muisca Confederation, the troops settled on the Bogotá savanna. De Céspedes was sent south, while the other troops went north, into the territories of the "zaque" of Hunza. De Céspedes reached Fusagasugá in May 1537 with forty infantry and 15 horses. On July 15, 1537, Juan de Céspedes conquered and founded Pasca, Cundinamarca. De Céspedes continued south and west from there through the Sumapaz Páramo into the territories of the Sutagao. He was accompanied by Juan López de Herrera and suffered from the cold climate. As a result of his bravery during this harsh conquest, De Céspedes was awarded the encomiendas of Ubaque, Chipaque, Quetame and Subachoque, to the east of and on the Altiplano Cundiboyacense. The encomiendas of Ubaque and Quetame were passed on to his son Lope de Céspedes.