Imagine, the oldest street in the New World. Imagine, walking the same cobblestone road as Christopher Colombus. Constructed over 500 years ago, Calle de las Damas, a half mile stretch of history in the Dominican Republic’s Colonial District in Santo Domingo, is indeed believed to be the oldest street in the hemisphere, Santo Domingo itself known as the oldest city of the New World.

Built in 1502, the street lives on as homage to Maria de Toledo, wife of Diego Columbus and niece of King Ferdinand, and the noble wives that accompanied her along that path to Mass. Diego Colombus, son of Christopher Colombus, was appointed Viceroy of the Indies in 1508, bringing with him his pious wife and their accompanying entourage. So impressed by the daily display of piety were the people of the Dominican Republic, they named the street in their honor, Calle de las Damas, Walk of the Ladies.

Today, strollers walking the historic street can explore the centuries old structures that were once home to figures important to the history of the Dominican Republic, and to the region. The Alcazar of Colombus, the 16th century castle built by Diego himself, houses a museum with period furniture and artwork. Casa de Bastidas, residence of Rodrigo de Bastidas, former governor of Santa Marta, Colombia and patriarch of the Bastida family (a family rival to that of Colombus in importance), now houses exhibitions, a library and school (where it once housed merchandise collected as tax). And for visitors wishing to do more than take a stroll through the Dominican Republic’s most historic district, the home of Santo Domingo’s founder Fray Nicolas de Ovando now stands as a small hotel noted for the only Gothic-Isabelline portal in the Americas, Hostal Nicolas de Ovando.