A lot of archaeological sites in Demir Kapija indicate the continuity of life from the neolithic and Iron Age through all periods of the antique and the Middle Ages to the modern settlement. The remainings of the fortification, the urban water supply, the many necropolis and sacred objects from the earliest phase of the antique speak about Demir Kapija as a multifaceted urban environment. It is also evident from the volume and the diversity of the entire archaeological material discovered in Demir Kapija, amongsty which is the image of the Greek picture made of ceramics dating from the classical period (the end of the 5-th and beginning of 4 th century BC)and

In 1940, during a construction work for expansion of the old road – at 200 meters before the tunnel on the way Varnici – a group of graves was excavated. The excavation contained painted greek vases, gold and silver jewelry including a beautiful “hidrija” (ceramic vessels in ancient Greece used to transport water with three handles) painted in the studio of the famous Athenian painter Midia portraying Dionysus with maenads from the late 5th century BC. With the excavations from 1948 – 1952 that were conducted by experts from former Yugoslavia new valuable findings have been revealed, among which one grave with white “lekiti”  , (specific grave vases that were characteristic for the Athenians). This shows that in Demir Kapija  a group of Athenians – probably mining and metallurgical specialists, craftsmen  and tradesmen – lived with their families. Their colony was located on  the rock Peshtera  above the hill Manastir (on the right bank of the river Vardar). This indicates that Demir Kapija in the antique  was the strongest market for export and – import in the Tikvesh area,  from where the  material and cultural developments and movements from the Aegean world have been distributed. The strategic  importance of Demir Kapija, in the antique noted –  as Stenae on the famous Pojtingerova map (the Roman road map of the world), which means crossing, gorge, ravin, and in the Middle Ages known as Prosek with  the same meaning (intersection, slit, crossing) is huge.  Here, every movement – from the north to the south and vice versa could easily be controlled, because that was the natural boundary between ancient Macedonia in the south and Pajonija in the north. There were two additional crossings, – surrounded by hard-traveled  paths through the hills of the dale Postralec,  south of  Prosek, at 380 meters  high Prevalec to the north end of  Juruchki Kamen. Both crossings were controlled by separate forts and long walls – barriers – clauses. The first population that lived in this area as confirmed in writing was Pajonite. Their colony was established on the left bank of the river Vardar  high  on the rock –  site called Markov Grad. This rock is high between 120 – 220 meters above the river and is almost inaccessible, except from the north side. There, a strong wall that served as a fence was built in the area of 14 hectare. There were also two smaller fortresses set on  the ridge Juruchki Kamen – north of of the colony,  which disrupted the enemy’s attacks from the north, as the only side where attacks could be possible. Here in the northern of the two forts, the coin of the Pajonian king Teutaj and of the city Akant was found, and this is now the oldest finding of this position  (5 th century).  The name of this town was probably Almana. The Roman historian Tit Livij noted that in 168 year BC, the last Macedonian king Persej traveled with a large army to the north in order to meet the Gauls. Moving along the Vardar road, near the city Almana on the coast by Aksij, he constructed a camp from where he sent a delegation to negotiate with the Gauls at the time when the Gauls had already arrived to the Osogovsko – Bregalnichkiot region, – in order to make them take his side in the war against Rome. The camp of the Macedonian army had to have undoubtedly – strong strategic position in case the strong and combative Gauls change their minds and attack from the north of Macedonia. Demir Kapija, with its strategic position, was best suited in this case. In early Roman time the local population left the high rock – Markov Grad and moved to the other side on the plain, on the other bank of- the embouchure of the river Doshnica in Vardar. The exploration found that here the houses from the late Hellenistic and the early Roman period were lying on older Pajonski graves. This coincides with the colonization of Philip V, – and continued under the Roman administration. The new town on the plains in that time was framed with defensive walls and covered an area of 10 hectares. Marble decorations of a temple, waterworks and drainage, graves, more tombstones and, a marble sculpture were excavated there. One temple excavated 3 km north of the ancient city near the Vardar route contained marble relief icons and small sculptures of Artemida and Dioskurite (2nd- 3rd century AC). All the colonies along the river Vardar, that are archeologically confirmed and can be marked as cities, had their own – name: -only the name Demir Kapija is not confirmed. There are three written monuments which show that Demir Kapija was a city: two of which are pedestals for a statues of Roman officials or creditable citizens from the 2nd and early 3 rd century, where only polis is mentioned, without the name of the city. The third monument is miljokaz from the time of Constantine 1 (early 4th century). On Pojtingerova map (the Roman road map of the world), – (the middle of 4 century AD) after Antigoneja is observed Stenae and that is why we use this name in the literature. In the period of the late antique, all these ancient buildings were still in use:,- with minor modifications they are in use even today. The new name of this place – Prosek occurred not later than the 10 th century which is confirmed by numerous archeological findings . In the 12 th and 13 th century two dignitaries ruled in Prosek – Dobromir Hrs and Dobromir Strez. The fortified city had an area of 17 hectare – Strezov Grad, separate from Gorniot Grad – Markov Grad with Chelevechka River, which housed fortified castle with three towers and a large rainwater. In Prosek there were two churches which are also confirmed by archaeological coins from 10-14 century

On the opposite side of the gorge there was one tower – tower of Postralec, and its goal was to control the narrow road near Vardar and one surrounding path confirmed with incised wheel cart in length of 15 metres – that oxen should be pulled from Krastavec high over Vardar. In 1385 it fell under the Turks and in the turkish documents from the 16th century is recorded as a village Demir Kapija, name which has survived till present day. Demir Kapija had a strong importance in the period of the antique as a micro-region with mineral resources. The averment scrap heaps of stones on both sides of the river attest that in the river Doshnica gold has been rinsing. Sheets of raw gold which have been rinsing here are found in the tombs of the dead in the village Chiflik. A few miles from the village Chiflik, near village Dren, ancient copper mines have been found. In the mining colony on the crest Peshtera by the Monastery leaden bullets as a direct confirmation for – melting minerals were found. It is one of the main reasons why the Athenians staid there. Access to the bearings of iron, arsenic, lead – silver and copper mineral in the middle pools of Kozuv led toward Demir Kapija upon the valley of the river Boshava up to its sources.

The spiritual culture – the religion – in Demir Kapija is marked by intense presence of indigenous cults associated with fertility, renewal of life and its continuity, and it appears very early, – first strongly influenced on the Greek and then on the Roman pantheon. For the region of Demir Kapija (the site Crkvishte), a group of distinctive monuments of the ancient cult is characteristic. They are probably of indigenous provenance – acres with “bukarioni” (referring to the skull of an ox, was a common form of carved decoration in Classical architecture used to fill the metopes between the triglyphs of the frieze of Doric temples). It is more or less acres with plastic representation of bull heads with horns and ears on which only the eyes and mouths are highlighted and marked. Their meaning on the one side can be connected with the cult of the ancient farmers, but on the other hand “bukarionot” – (referring to the skull of an ox was a common form of carved decoration in Classical architecture used to fill the metopes between the triglyphs of the frieze of Doric temples), can be treated as a symbol of the beginning and of the strength. It can be considered to be a representation of Dionysus, but also a replacement of the sacrificed animal that is given to Zeus as the highest divinity. The sanctuary of Aphrodite in the cave Zmeovec in the village Dren (2 nd – 1 st century BC) with fragments of sacral terracotta which mostly belong to Aphrodite – but there are also samples that belong to the Demetra and, – Athena (female principle, women divinity associated with the fertility and desire for birth) only confirm the strong influence of the Aegean world. The marble relief from the village Bistrenci displays maenads, triads or “bahanatkinji” from the Dionysus escortin in the dance – in abundance of floral motifs especially ivy and grapevines, -two completely dressed female figures are handed over to the dance – enthusiasm expressed by the body movement, – speaks about the strongly widespreaded cult of the god Dionysus. The cult of the “Dioskurite” (twin brothers, Castor and Pollux or Polydeuces together known as the Dioskouri) during the Roman period of the 2 nd -3 rd century is attested in finding the sculptural group of marble in their sanctuary in Demir Kapija where in the middle a female goddess, probably Demetra, is standing and her companions “dioskurite” (were twin brothers, Castor and Pollux or Polydeuces together known as the Dioskouri), – are next to her. In the same sanctuary three votive plates are discovered. Demetra is – a goddess of the nature and animals and patroness of the marriage. “Dioskurite” (were twin brothers, Castor and Pollux or Polydeuces together known as the Dioskouri), are the link between the upper and the lower world, light holders and savior of the mankind. All these votive plates and the whole sanctuary belong to the 2 nd – 3 rd century. During the period of the Roman antique a cult towards the deceased was developed, and it witnesses for the construction of mausoleum – “herooni” (or heroonat is a sanctuary of hero honored in a special cult in ancient religions) or memory, as is the “heroonot” (or heroonat is a sanctuary of hero honored in a special cult in ancient religions) in the village Barovo. The beginnings of the Christianity in Demir Kapija today are visible on the ground. Archaeologically they can be followed through the remainings of the foundations, the walls of the early Christian objects – such as the basilica with a small church on the site Crkvishte and the basilica on the site Manastir, just in front of the tunnels. The early Christian basilica dates from the 4 th -6 th century, and the small medieval church on the central area of the basilica with the necropolis around it dating with jewelry and coins from the end of 9 th-15 th century.In the sources of 11 th century, Demir Kapija was noted as a church center within the frames of the Meglenska diocese. Later on, when in the first half of the 14 th century Prosek falls under the Serbian rule, the church was dedicated to the Virgin and the church property was given to a Hilander for ruling. It was ruined by the Turks in the first half of the 15th century when the whole territory of Macedonia fell under Turkish rule and since then it ceased to exist.