Stobi or Stoboi, was an ancient town of Paeonia, later conquered by Macedon, and finally turned into the capital of the Roman province of Macedonia Salutaris. It is located near Gradsko, on the main road that leads from the Danube to the Aegean Sea and is considered by many to be the most famous archaeological site Macedonia. Stobi was built where the Erigon (Crna River) joins the Axios (Vardar), making it strategically important as a center for both trade and warfare. The city was first mentioned in writing by the historian Livy, in connection with a victory of Philip V of Macedon over the Dardani in 197 BC. In 168 BC, the Romans defeated Perseus and Macedonia was divided into four nominally independent republics. In 148 BC, the four areas of Macedonia were brought together in a unified Roman province.

During Roman times Stobi was the capital of the Roman province Macedonia Salutaris. Emperor Theodosius I stayed in Stobi in 388. Late in the 5th century the city underwent a terrible turn of events. In 479, it was robbed by Theodoric, an Ostrogothic king. The citizens reconstructed the city, but in 518 it was struck by a powerful earthquake. Avaro-Slavic invasions in the 6th century destroyed the city's economy and infrastructure.