Ruttenstein Castle was first time documented in 1209, in a deed issued by Duke Leopold for the Baumgartenberg Monastery, where it is mentioned under the name Rotenstein. The existing structure of the high castle, however, suggests that the castle is significantly older. The construction period likely falls in the first half of the 12th century, although this is not documented. It is probably a foundation of the Counts of Clam-Velburg.
The walls of the formerly massive pentagonal keep are now only partially preserved, tapering to a point and visibly towering over the site. The former residential wing in the west retains three of its walls. Above them, a viewing platform has been constructed, accessible via wooden stairs. Clearly recognizable, though also only partially preserved, is the early Gothic castle chapel located near the stone steps to the residential building. The main castle itself was protected on the north, south, and east by a mighty ring wall, which is still partially preserved today, and from which seven wall towers protruded.
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.