In spring 1985, the oldest evidence of human habitation in Pieniny was accidentally discovered near the Obłazowa rock, in the vicinity of Nowa Biała village. During excavation works, tools made out of stone that date back to c. 10-9 thousand years B.C. were found. This archaeological camp has been linked to the late Paleolithic Federmesser culture. Shortly afterwards, excavations revealed signs of an entrance to a cave which had become completely filled-in. Scientists suggested that the cave might have been inhabited and began studies which were to last for 7 years. The results exceeded all expectations.

In Obłazowa cave, the oldest human bone – a thumb’s phalanx - was discovered, dating back more than 50 thousand years to Neanderthal Man. This was the very first of such discoveries in Poland. Further research of the materials discovered in the cave has shown that the cave was also inhabited on several occasions later, c. 40-36 thousand years ago.
Another group of settlers appeared in the Obłazowa area about 20 thousand years ago. They were the miners who used to extract the Pieniny radiolarite. On excavating the cave scientists discovered the oldest mining tools ever found in Poland – two wedges made from reindeers’ bones and articles made from flint. One tool was made from “chocolate” flint. This kind of flint used to be mined in the area of Krzemionki Opatowskie and it is still puzzling just how the tool came to be found in Pieniny. The most precious of all cave findings was a boomerang made from a mammoth’s tusk, which dates back to 18 thousand years B.C. A reproduction of this boomerang is exhibited in the Pieniny National Park Headquarters in Krościenko n/D. New findings have been preserved since the turn of XV and XVI centuries including fragments of vessels, weights made from lead, a crossbow’s bolt,. Fishermen, who used the cave as a shelter, probably left these articles.

Traces of Paleolithic man have been also found in the Pieniny Właściwe. An archeological excavation in Sromowce Niżne at Kąty revealed a relict camp where radiolarite used to be carved on a large scale. Also, some tools made from “Baltic” and “chocolate” flint were found there.  This site, which dates back to 13,000 – 10,000 B.C., is regarded as unique in terms of representative traces of Magdalenian culture in Poland.
The next chapter in settlement history is determined by collections found at the foot of Three Crowns Massif – at the mouth of Macelowy Potok valley (Macelowy stream). This archaeological find dates back to 9,000 B.C. and has confirmed the presence of hunter-gatherers, representing the end of the Paloeolithic.
A variety of stone tools, including tools which might have served as spear heads and implements for carving bones and cutting skin (e.g. scrapers) have been found.  On the basis of the site’s locality - near the Dunajec river - it is claimed that camp inhabitants caught fish.

In the Neolithic the Pieniny Mountains were not inhabited permanently. Archeological findings from that period suggest either transient cave settlements (at Haligovce) or open-air settlements (indicated by limited collections of stone works). It should be noted that no pottery, which is characteristic for most Neolithic localities within the Polish Carpathians, has been found. Palinological studies suggest that at the turn of Neolithic and Bronze Ages, groups of shepherds which used to exploit the forest resources (as evidenced by forest thinning) appeared in the Pieniny area. Some diverse individual objects from the Bronze Age have also been found in the Pieniny area.

The Middle Ages left some remains behind in the Pieniny, too. There is no doubt that in those days fortified settlements were in existence on Zamczysko mountain near Sromowce Niżne village, on  Jarmuta mountain near Szczawnica and probably in the Homole ravine. Only small groups of settlers occupied the alluvial areas of the Dunajec river, especially in the vicinity of Krościenko (where the oldest signs of their existence have survived) and at Sromowce Niżne and Wyżne.
The Middle Ages are associated with the creation of a diverse range of scattered settlements. From the early Middle Ages to the mid-13th century the colonization of the Pieniny and Podhale regions was non-intensive. Only by the peak of the Middle Ages had the main settlement wave reached the Pieniny region, when two distinct colonization trends were evident – the “Polish” and “Hungarian” ones divided by the Dunajec river.

The origins of settlement in the Polish part of the Pieniny mountains are directly associated with the Sisters of St. Clare convent in Stary Sącz, founded in 1280. The Pieniny castle on the Zamkowa mountain (the Castle mountain) had been built a little earlier. It is believed that this castle was founded by Princess Kinga, wife of Prince Bolesław Wstydliwy (Bolesław “the Bashful”) and  built between 1257 (when Prince Bolesław granted the Sącz area to Kinga) and 1287 (when the Mongolian attacked Poland).

The first village which was set up by the St. Clare nuns  in accordance with Magdeburg statutes of local self-government and mentioned in a document dated 1323, was Sromowce Wyżne. Originally the village was known as Przekop (the word “przekop” means “logging” and is derived from the way in which tree logging was carried out in order to strengthen and protect the Dunajec river crossing).

In 1346, King Kazimierz the Great granted a town charter to Krościenko village. At the same time Czorsztyn castle passed to the King’s rule. Simultaneously, “starostwo” – royal unitary district made up of Krościenko, Czorsztyn and Sromowce Wyżne and Niżne, Maniowy, Grywałd, Haluszowa, Tylmanowa, Ochotnica, Szczawnica and Kluszkowce villages came into existence.

By the turn of the XIII and XIV centuries increasingly intensive settlement had reached the other side of the Dunajec river, at a place called Zamagurze. The colonization of the area was due to Germans from Saxony who had been brought there by the Berzeviczy family – owners of Niedzica. They settled in the vicinity of Dursztyn, Falsztyn, Frydman, Krempachy, Łysa, Szwaby (now Red Monastery) and Lechnica villages. That Spisz-German settlement trend played an important role in converting Polish villages into self-government according to the Magdeburg statutes.

By the turn of the XIV and XV centuries the Wallachian people (ancestors of later Rusnaks - Łemkos) swept the Pieniny area, moving along the Carpathian ridge from the east. After traditionally leading a nomadic life, they started to settle permanently. The Wallachian shepherds occupied the higher grounds with poor soils - unsuitable for agricultural crops but convenient for animal breeding and pasturing. Foundation of many villages took place at that time, for example: Jaworki, Szlachtowa, Czarna and Biała Woda (White and Black Water) and on the Slovak side - Lipnik, Jarabina, Kamionka, Straniany.