Tolentino is a historic town with well-preserved medieval buildings with some interesting churches. The monastery of Chiaravalle, around which a nature reserve has been established, is very famous.
The town already existed in Roman times, and monuments from that period can be seen today in the local Archaeological Museum. However, it experienced its greatest development in the Middle Ages, being an important local trade and craft center.
The historic buildings with several churches have been preserved in the city center. The most valuable of them is the thirteenth century basilica of St. Nicholas, to which a baroque façade was added in the 17th century. Also from the 13th and 14th centuries the local churches of St. Francis and St. Katerwiusz. The latter is part of a Benedictine monastery and the place where the carved sarcophagus of St. Katervius from the 1st century
Outside the city walls is Tolentino's biggest attraction, surrounded by the Abbadia di Fiastra Nature Reserve, the Cistercian Abbey of Chiaravalle. Romanesque buildings, dominated by a polygonal tower, today include The Wine Museum and the Museum of Agricultural Tools.