Some archaeological excavations suggest the Kratovo area was settled in Roman times or earlier, but it did not achieve great importance until it fell under the Kingdom of Serbia in the late 13th century when gold, copper, lead, silver, and iron were mined in and around Kratovo. Coins were also minted in the town during Serbian rule.

In 1390, Kratovo was taken over by the Ottomans. It would remain within the Ottoman Empire for the following five centuries. By the 16th century, it was among the most important mining centers of the Ottoman Europe. It was home to many wealthy and educated men. The mint of Kratovo, opened in the end of the 15th century, became the second-largest producer of coins in the empire. Some of these coins are on display at the Museum of Archaeology in Skopje.

The mint of Kratovo ceased operations around 1660. Seven mines, however, were still active in the town and its vicinity until the Hapsburg forces, after temporarily taking the town, retreated and burned it down. Mining activity in the region then shifted to Probištip and Zletovo. It only recovered within Kratovo around the early 1800s, though on a smaller scale. Its population was around 5,000 to 6,000. After the mines finally shut down for good in 1882, the population fell to 4,500, half of which were Turks. After Kratovo was taken by the Serbian army in 1912, much of the Turkish population left, leaving the town with under 2,000 inhabitants.

Now part of North Macedonia, Kratovo has about 6,900 residents and is the seat of the municipality of the same name which includes 30 surrounding villages. Virtually all of the residents of the municipality are ethnic Macedonians and Macedonian Orthodox Christians.

• 42.07777122.1765611 Bus Station (Кратово Автобуска Станица). Kratovo's bus station is in the western end of town, where St George of Kratovo Street splits off from highway R1205. There are daily bus connections between Kumanovo, Skopje, and Štip. This is the cheapest method of getting into town. 

A taxi from Kumanovo should cost no more than 1,500 denars, while a ride from Skopje shouldn't cost much more than €30. Make sure to agree on the price before getting into the cab.

Bridges have connected the town across the Kratovo River and its tributaries for centuries. Five of the medieval stone bridges remain.

• 42.07536422.182514 Argulički Bridge (Аргулички мост). Crossing a tributary of the Kratovo River in southern Kratovo, this stone bridge consists of a single rounded arch. (updated Aug 2016)
• 42.07859322.181855 Čaršiski Bridge (Чаршиски мост). Located between the Grofčanski and Jokširski bridges, the Čaršiski Bridge has a rounded arch unlike the two neighbouring it which have pointed arches. (updated Aug 2016)
• 42.08016322.1840936 Gornoamamski Bridge (Горноамамски мост). The easternmost of the bridges. (updated Aug 2016)
• 42.07821822.1811657 Grofčanski Bridge (Грофчански мост). The westernmost of the medieval bridges, the Grofčanski Bridge has two arches, under one of which the river runs. The bridge was built in the early 1700s. (updated Aug 2016)
• 42.07932722.1824558 Jokširski Bridge (Јокширски мост). The stone single-arch bridge connects the tannery neighborhood to the Sultan Murat neighborhood. (updated Aug 2016)
• 42.07548322.1843379 Radin Bridge (Радин мост). This bridge is newer than the other five, having been built in 1833 by Skopje nobleman Havzi Pasha. It crosses one of the Kratovo River's tributaries in the southern end of town. (updated Aug 2016)

Kratovo once had 12 towers, five on the right side of the river and seven on the left. Today, six remain including Hadži Kostov Tower and the five below. Of these, the Clock Tower is the easiest to access as it houses exhibits of the Kratovo City Museum.

• 42.07912922.1817510 Clock Tower (Саат кула). One of the six remaining towers of the Middle Ages and Ottoman period. Built in 1372, it is divided into three floors. The uppermost was used as a home for the local Turkish beys (lords). The tower, now held by the Kratovo City Museum, is open to the public and contains exhibits. The terrace at the top is also open to visitors, providing views of the town and its surroundings. (updated Aug 2016)
• 42.07696822.18263311 Krste's Tower (Крстева кула). This square tower is in very good condition. On the entrance side, it has four windows and two balconies. (updated Aug 2016)
• 42.07822222.17986812 Simikj's Tower (Симиќева кула). This tower is located north of the Kratovo River and stands 13 m (42 ft) high and 6 m (20 ft) wide. (updated Aug 2016)
• 42.07696222.18238413 Srez Tower (Срезка кула). Located just west of Krste's Tower, the Srez Tower is in rougher shape than its neighbour and could use a new roof. (updated Aug 2016)
• 42.07832222.18093914 Zlatko's Tower (Златкова кула). Built in 1365, the tower is named after its last owner Georgi Zlatkov. The rectangular tower with three floors stands 6 m (20 ft) tall. (updated Aug 2016)

Kratovo Municipality contains several historic villages. Important sites within Kratovo Municipality:

• 42.12444422.05027815 Stone Dolls of Kuklica (Камени Кукли) (village of Kuklica, 11 km west of Kratovo). This natural wonder, consisting of 15 larger (10 m / 32 ft tall) and 120 smaller stone pillars, was probably created by erosion and other climate influence. However, the legend connected to this phenomenon says that the figures are in fact wedding guests who were turned into rocks. (updated Oct 2017)

• 42.08371321.98596716 Cocev Kamen (Цоцев камен), village of Šopsko Rudare. Cocev Kamen is within Kratovo Municipality but, because of some mountains, is a shorter drive from Kumanovo than from Kratovo. The hilltop cave site of volcanic origin may have been inhabited as early as Paleolithic times. Some of the walls are painted, similar to such caves found in Bulgaria and Italy. It may have also been used as an astronomical observatory. (updated Oct 2017)
• 42.08166721.96055617 Golemo Gradište (Големо Градиште), village of Konjuh. This archaeological complex contains remains of sites dating from Late Antiquity and the medieval era. It is thought to be the location of the late Roman fortified town Tranupara. Situated on a hill near the Kriva River, the more prominent ruins include an early Christian church from around the 4th century and a medieval church from the 14th century. The former mostly consists of short walls and foundations; a church dedicated to St John the Baptist was built next to it in 1955. The latter is largely still standing and has had a new roof installed atop it. Traces of the original frescoes as well as some decorative ceramics are found inside. While the original dedication is unknown, it has been named after St George. (updated May 2019)
• 42.06527822.162518 Church of the Holy Mother of God (Црква „Св. Воведение на Пресвета Богородица“), village of Šlegovo. In the centre of the historic village of Šlegovo is this 1861-built church. Several old icons are within the church, including a couple that predate its construction. Made entirely of stone, the church features a long porch with several arches and a very nice bell tower. (updated May 2019)
• 42.07277822.01611119 Church of Saint Nicholas (Црква „Св. Никола“), village of Šopsko Rudare. This site has two churches, an older one dating from the 16th century and a newer one built in 1939. The older church is simple on the outside with a pitched roof but contains significant frescoes on the inside. The newer St Nicholas is a prominent structure with a large dome, though it is in surprisingly rough shape. (updated May 2019)