Taggenbrunn Castle site was already used as a Celtic-Roman hillfort settlement in the 6th century BC. The first mention of current castle dates from 1142. The castle was destroyed in 1258 in a rebellion agains Duke Albrecht I and rebuilt ten years later. Later the castle was owned by the Holy Roman Empire and archbishopric of Salzburg. The castle was expanded in 1497-1503. In the 17th and 18th centuries Taggenbrunn was left to decay. Today there is a wineyard and restaurant.
Stobi was an ancient town of Paeonia located near Gradsko. It is considered by many to be the most famous archaeological site in North 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.
Stobi developed from a Paeonian settlement established in the Archaic period. It is believed that in 217 BCE, Philip V annexed Paionia during his campaign against the Dardani who had entered Bylazora, the largest Paeonian town.
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. In the reign of Augustus the city grew in size and population.