Church of Saint Petka

This 14th-century monastery was a religious center and an educational and cultural hub. Its main church was built upon ruins of an older basilica, though it was demolished and rebuilt in the 16th century. Its fresco work was also done around this time. The stone church is most of what remains from the monastery's peak as a literary and translation center. It is in somewhat rough condition and has not had a church service in years.

This church was built sometime between the 14th and 16th centuries. The square-shaped church has some interesting details in architecture, particularly in its arched windows. Capped with red shingles, the church also has a stone bell tower.

A medieval monastery with its main church dedicated to Saint Athanasius. Once abandoned around 1900, it now boasts a healthy monastic life. Until 1998, it changed from a male to a female monastery. The main church features a large porch, unique to the Demir Hisar region, and an attached bell tower. It was built in 1617 and its fresco worked was also done around that time. The grounds also contain a historic library.

Situated in the valley of Ilino Mountain just west of Slepče, this large monastery complex was most likely established in the late 14th century. The main church as it exists today, however, was primarily built in the 19th century. Following the Ilinden Uprising of 1903, the monastery was attacked by the Ottomans.

This church was built in 1838 in the middle of Velmevci. It is a large, white three-nave church. Its iconostasis was completed in 1873, while its frescoes were done in 1874. The church is historically significant as the oath of the Demir Hisar Conspiracy was made here in 1880.

Construction on this museum began 100 years after the Smilevo Congress of 1903. It was completed the following year and is divided into five sections: the memorial room of the Smilevo Congress, Smilevo in the Ilinden Uprising, the Dame Gruev memorial room, the Partisan memorial room, and the Smilevo ethnological room.