The old part of Kratovo is connected with six bridges, built over the deep and steep river valley. Only one bridge has two arches, the rest are single-arch bridges. “Radin Most” (Rada's Bridge), which is 40m long and nine brothers and an amazing legend tells its sad story. The nine 23m high, is the most well-known bridge. The bridge was built by brothers were trying to build the bridge for many years, but the bridge kept collapsing every morning. Someone told the brothers that, if they buried one of the wives in the foundations of the bridge, it would remain solid. The brothers agreed that the wife who came first that morning to bring them breakfast would be the one to be buried. The older brothers told their wives not to go to the bridge the next morning, just the youngest one said nothing to his wife Rada. When the woman came in the morning, they buried her in the bridge, but left her with one breast out so she could feed her baby, who was just three days old. The bridge never collapsed again and has resisted time since.
The town once had 12 towers, but unfortunately only six of them have been preserved till present day. Certain documents state that the towers were built by the renters of the Kratovo mines, which were used for living and storing away the ore. The most attractive towers are Simitceva Tower and the Saat Kula (the Clock tower).
Lesnovo Monastery is located in the surroundings of Kratovo, on Mount Bukovec, at an altitude of 1,118m. Gavril from Lesnovo village is believed to have founded the monastery. He dedicated the monastery to St. Michael Archangel. In the past, more than 200 monks lived in the monastery.
According to a manuscript from the 19th century, the monastery library used to hold more than 20 loads of religious manuscript. The fresco painting in the church dates from the time of its construction and was done by painters Sebasto, Mihail, and Marko. The iconostases were done by the famous Macedonian wood-carvers - Petre Filipovski Garka and brothers Negre and Makarie Frckovski. The tree growing in the yard of the monastery is believed to be over 580 years old.