African swine fever (ASF) has been detected in many European countries since its introduction in Georgia in 2007. Serbia suffered its first case of ASF in the domestic pig population in 2019. At the beginning of 2020, ASF was detected in wild boars in open hunting grounds in the southeastern region of the country in districts along the country’s borders with Romania and Bulgaria. Since then, all ASF outbreaks in wild boar were clustered in the population located in the same bordering areas. Despite the newly implemented biosecurity protocols for hunters in 2019, ASF was detected for the first time in June 2021 in the wild boar population located in an enclosed hunting ground in the northeast region of the country. In this study, we reported the first ASF outbreak in a wild boar population located in an enclosed hunting ground in close proximity to the Serbian–Romanian border. The epizootiological data on the field investigation of the ASF outbreak, with descriptions of the clinical signs and gross pathological lesions detected, including the total number as well as the estimated age, sex, and postmortem interval, were analyzed. Clinical signs were detected only in nine diseased wild boars, while in total, 149 carcasses were found in the open and enclosed part of the hunting ground. In addition, 99 carcasses from which samples (parts of spleen or long bones) were collected for molecular diagnostics (RT-PCR) were confirmed as ASF-positive. The results of the epidemiological investigations indicate the central role of wild boar movements as well as the constant risk of human-related activities in the countries bordering area.