Dolorosa Street — Street of Sorrows — is one of the original thoroughfares of Spanish colonial San Antonio, and its name carries three centuries of history. When Spanish Governor Martín de Alarcón laid out the settlement of San Antonio de Béxar in 1718, he established a grid of streets connecting the presidio, the civil plaza, and the river. Dolorosa was among the first named streets, and its name — referencing the sorrowful mysteries of the Catholic rosary — reflected the intensely religious character of the colonial enterprise.
The street served as a route for religious processions from the earliest years of the settlement. On feast days, the Stations of the Cross would be enacted along the street, with parishioners moving from one station to the next between the cathedral and the river. During the siege of the Alamo in 1836, Dolorosa Street would have been within range of the gunfire and cannon exchanged between the Texian defenders and Santa Anna's forces.
After Texas independence and American annexation, the street's character changed — it became a commercial thoroughfare lined with shops serving the growing city. Today it runs through the heart of downtown, connecting the Spanish Governor's Palace to the civic center, threading past the oldest layers of the city.