Numerous tombs, from the 8th to the 4th centuries BCE, attest to the presence of the culture of the Piceni at the site of today's city, Roman Tolentinum, linked to Rome by the via Flaminia.

From the end of the 14th century, the commune passed into the hands of the da Varano family and then the Sforza, before becoming part of the Papal States until the arrival of Napoleon.

The Treaty of Tolentino between Bonaparte and Pope Pius VI was signed in the city on 19 February 1797: this imposed territorial and economic strictures on the Papacy.

[3] In 1815, at the battle of Tolentino, Joachim Murat was decisively defeated by Frederick Bianchi at the head of Austrian forces, resulting in his abdication.

The nearest major airport is Falconara (Ancona), about 100 kilometres (62 mi) from Tolentino but linked by highway, and there is a tiny airstrip for ultralight aviation in the town's immediate surroundings.