Kurşumli Han ruins

Prilep's central square is named for statesman Metodija Andonov-Čento, the first President of the Socialist Republic of Macedonia. The open space is bounded to the east by the Old Bazaar, to the north by Goce Delčev Boulevard, and by various buildings to the south, including the 11th of October Museum, and west. An equestrian statue of famed King Marko sits in the square facing the clock tower.

A prominent statue of Alexander the Great stands across the boulevard from Čento Square, beside a park area. The ancient Macedonian king is holding a spear in one hand and a shield in the other.

The concept of this museum dates back to 1948 when documents, photographs, and art were showcased in a former inn. In 1952, it moved to an early 20th century building that was used by the Bulgarian fascists as a police station. The museum is divided into three halls, the first of which showcases pieces related to events prior to 1940 in the Prilep area. The second exhibits pieces from 1941 and the beginning of the National Liberation War, while the third hall showcases the events of 11 October 1941.

Prilep has a pleasant, compact, and well-maintained bazaar with orthogonal streets. It is likely the country's third-largest, following those in Skopje and Bitola. A small square within the bazaar features a fountain with a monument of Itar Pejo (Sly Peter), a folklore character who is considered to be a native of Prilep. Itar Pejo is presented as a typical Macedonian who always manages to outwit a typical Ottoman named Nasreddin.

Towering above the Old Bazaar, this is the most beautiful clock tower in Macedonia. Built in 1826, it stands 55 m (181 ft) tall. It first received its clock in 1858.

Built in 1475 atop an older religious building, this mosque was the oldest in Europe to having a double balcony on its minaret. Following protests in 2001 against the massacre of ten Macedonian soldiers by Albanian rebels, the mosque was set afire and now sits in ruins. Most of the minaret remains, as well as many of the walls. The ruins are unprotected and open to public trespass.