The Malesh region has been inhabited since pre-historic times, which is verified by the remaining of the settlements and the mounds .    There is almost no research done on the large number of registered archeological localities , thus it is impossible to say what time they date from.    The conducted field work resulted in dome findings that indicate a possibility for relative archeology.  According to the folk legend the name Maleshevo is of Iliric origin and comes from the words mal-mountain and malesi- mountainous area.  Some of the scientists believe that the toponyms Malesh, Maleshevo i.e. Malesevo come from the Old Slavic words mal les, which means small forest, small mountain.

In the 4th century Maleshevo is part of Philip and Alexander the Macedonian's state.  After the collapse of their empire, Macedonia as well as Maleshevo became part of the Roman province Macedonia.  In 6th and 7th century the territory of Maleshevo is inhabited by Slavs.   On this same territory Konstantin the Philosopher created the Cyrillic alphabet.  After the  collapse of Samoils's Macedonian Kingdom Maleshevo falls under Byzantine rule.   The first mentioning of the name Maleshevo in the written sources is in a written document of the Byzantine Emperor Vasilij II from May 20th 920 where he speaks of the number and content of the parishes of the Ohrid Archbishopry .  A hundred years later Maleshevo is mentioned by the Arabic writer of travel books Idrisi.  Some scientists, such as Gae Tser believe that in the 9th century the parish from Morozvizd (Morodvis) was transferred in Maleshevo, a town that was located along the upper flow of the River Bregalnica, in the embrace of the ancient beech and pine forests.  According to Vasilij's document this town includes two regions: Maleshevo and Pijanec.  Since 1334 Maleshevo became part of the Middle Ages Serbian state, and after that it was part of Konstantin Dejan's feud and it is believed that in 1394 the town Maleshevo  was destroyed by the Turks.  After the Balkan wars and the First World War Maleshevo is included in the Kingdom of Serbians, Croats and Slovenians.  Today Maleshevo as a geopgraphical term refers t an area of about 80.560m2 and it includes two municipalities - Berovo (town Berovo and the rural settlements Rusinovo, Vladimirovo, Ratevo, Dvoriste, Smojmirovo, Machevo,Budinarci and Mitrashinci) and Pehchevo.