Cultural wealth of Stip is enormous. Stip has developed a network of cultural institutions that are important: NI Institute for Protection of Cultural Monuments and Museum, where collections are kept and funds in the field of archeology, ethnology, history and art.

NI Library “Goce Delcev”, which today works by modern standards and with the largest scope of publishing activities. More than 20 years within the library works and literary club Iskra;

House of Youth includes cultural activities are interesting for youngsters. Astibo Jazz Festival;

NI Center for Culture “Aco Shopov” where as stem forms work: Children's Drama Studio and Art Studio. Within the center is successfully functioning the National Theater. The interest of tourists certainly will be attracted and the gallery of icons in the church of St. Bogorodica.

Stip is famous for Festival of fun melodies Makfest. 24 edition held in the organization of local self-government. Stip is known for Stip’s cultural summer.

Bezisten Art Gallery is a cultural monument which dates from the second half of the 16th century when he served as the main bazaar for the sale of luxury goods. Today is the most appropriate space for music concerts and art exhibitions.

Between the two rivers, 150 meters high on the rocky hill over the town, the Stip Fortress, or better known as the Isar stands guard. People say that the fortress was built by King Marko, while his sister Maria was building a road and bridge through the canyon so that the people could cross the Bregalnica River. Even though she advised her brother to build things that would be useful to the people instead of a fortress that will exist only during his life time, King Marko was stubborn and built the fortress. The prediction of the clever Maria came true; the fortress was of short duration. For a long time after that, the people spoke of Maria’s good deed, singing a song whenever they passed the road through the canyon that she built, while the fortress of King Marko was soon in ruins.

The Museum was formed in 1950 as a city institution, but in 1955 it was transformed into a regional museum. Attempts to make any short list of biggest advantages and successes of city’s museum is difficult job. It is not simple, because the museum posses many collections in the area of archeology, ethnology, history, art history and modern art.

Main activities of the city’s museum in Stip is to explore, discover and preserve historical material, professional protection of archeological material and protection of the city monuments with large historical value. Among other activities, people in the city’s museum also take care for church galleries, and reconstruction of ancient city of Bargala.

During work on the pipelines, a settlement from the earliest Neolithic phase, the only of the kind in Macedonia, has been unearthed near Stip. A team of archaeologists working in the field near the village of Krupiste has found the settlement at the Grncarica locality.

One of the oldest settlements in Stip is Novo Selo. Although there is no accurate data for the period of formation of the settlement, so it can be assumed that, as a separate settlement Novo Selo existed before the thirteen century. From the time of its formation, in Novo Selo, lived exclusively Christian population. This confirms the census of 1519, under which lived here 21 Christian families.

Macedonian architecture is very unique and can be seen in many structures around Stip. Historical  and legendary New Village has many of the traditional houses. It remain as national treasure because of it’s museum value. On the way to city spa Kezovica, many of the houses in traditional old macedonian architecture can be seen. Together with the icons gallery, it is a place with large capacitiy for spiritual venture. It is unforgetable and eternal city of Stip.

Old city clock is monument of culture from 17-th century. It is under protection of the state. Citizens recognize city clock as “Begova kula” or Tower of the Beg.According some historical material, the clock was built by a Turkish ruler (beg) that lived in the city. But his name remained unknown.He built the clock tower in order to protect his family during crise situations. That is why on the top of the tower there was a gun-room and terrace. A century later, a clock mechanism was placed on the top of the tower. Part of the tower was destroyed in 1934. Some thinks that it was because of security reasons, some said, it was result of some disturbances caused by citizens’s revolt because the clock was too loud.According an old document by the clock keeper, the tower was built in 1650 and it is related with a legend. A Turkish beg was in love in beautiful girl Anka. He wanted to take her and made her a bride. The girl refused that, and managed to keep that way for a long time. She promised to marry him only if he left some monument valuable for the city. She suggested to build a clock tower. Anka tought that the Turkish beg will gave up, but because he was madly in love, for very short time he managed to construct the tower and married the beautiful Anka from Stip.

The Husa Medin Pasha Mosque was built on a hill in the left side of the town. It is known as the church of St. Ilija, because it is believed to have been built on the foundations of an ancient Christian religious place.
According to the legend, Husamedin Mehmed Pasha built the mosque in the 17-th Century on the foundations of a church from the 13-th or 14-th Century that was dedicated to St. Ilija. Next to the mosque is the grave of Husa Medin Pasha.

Among the buildings in the central part of the town of Stip, there is a building outstanding with its architecture, typical for the Medieval Islamic trade centers. It is the Bezisten (Turkish word for market place). The time of its construction cannot be precisely determined. The Bezisten was used as the main market place where trade and selling of various goods was going on during the time of the Turkish rule in these areas. Considering this, we may suppose that this building dates from 16-th or 17-th Century. It was burned down during the war between Austria and Turkey.

The Bezisten in Stip has a stone construction with a rectangular basis that is divided into three separate rooms covered with vaults with massive domes rising above them. There are glass holes on them that allow for the daylight to penetrate the interior space and contribute to the noble ambient of the Bezisten. Today, the Bezisten is used as an exhibition space of the art gallery.

In the yard of the church of Holy Mother of God in Novo Selo (New Village) is a school where revolutionary Goce Delcev used to teach. Next to it is the house where the revolutionary lived. Today it is privately owned, but restored in authentic style.

The school was named after the great Macedonian revolutionary hero. After opening of the University of “Goce Delcev”, these school was given to the University. After reconstruction that will preserved the old and historical look, in the building will be placed the top officials of the Univeristy.