The old Tolentino - “Tolentinum” - is situated on a hill round base, at the foot of which Chienti River flows. Tolentino is in a territory of ancient settlement; archaeological studies show the presence of hunters in Lower Paleolithic, as well as the civilization is well attested in the Iron Age necropolis of Tolentino (sixth century BC), which has funeral finds giving signs of the presence of a warrior society, for presence of weapons, bronze vessels, potteries and various ornaments in tombs. The cemeteries of Marches were well described by archaeologists; they consist of graves without overlap, and the deceased was found in a crouching position with his head resting on a stone. As regards the Roman penetration, studies pointing to deduction of colonies in  Marches, including "Tolentinum", around the third century BC (For these aspects, see G. Buti-G. Devoto, “Preistoria e Storia delle Regioni Italiane” [" The Prehistory and History of Italian Regions"] , Florence, Sansoni, 1975, pp. 81-86).

With Regard to “Tolentinum”, the question of origins is quite complex, and probably the place, though widely known to the Latin literary tradition (Pliny the Elder mentions in fact the inhabitants of Tolentino, calling them" Tolentinates "), it was once inhabited by peoples from various places of origin; in fact, scholars suggest several people present in “Tolentinum”, the Illyrians, Ligurians, Umbrians, Picenes, and Etruscans too. Moreover, in past centuries, a famous humanist native of Tolentino, Francesco Fidelfo (1398-1481), studying the etymology of name, stated that Tolentino had Greek origins: "[...] Tolentinum vere Graecorum esse Coloniam, ut Anconam et Auximum et alias plerasque Piceni urbes; nome ipsum declarat: nam 'Tolentinum' graece 'Rotundum Intensum' significat. Talis illius situs, quae a rotunditate tendit [...]". Or: "[I think] Tolentino was a colony founded by the Greeks, as Ancona, Osimo, and many other cities of ‘Piceno’; the same name says it clearly, because, 'Tolentino', in Greek, means 'tending to round'. And, in fact, the site of city is just like that, because it tends to round ... "(the document is in Carlo Santini, “Saggio di Memoria della Città di Tolentino” [" An Essay of Memories of the Tolentino City] , Macerata, 1789, pp. 4-5).

G. Semmoloni notes, however, that "[...] the most widely accepted etymology is from Illiric 'tul-in', Etruscan 'tular-', meaning 'border' and it alludes to the border to which trans-Adriatic migrations came; however, the term 'Taulentinoi' is attested in Illyrian documents [...]" (See Giorgio Semmoloni, “Tolentino. Guida all'arte e alla storia” ["Tolentino. Guide to art and history,"] Tolentino, 1988). In accordance with this interpretation, then, "Tolentinum" means a "border town" and not, as proposed by F. Fidelfo, a "City tending to round". In Roman times, the city was at first a Colony and then "Municipium"; in the Middle Ages it was constituted as a municipality in the mid-twelfth century; in fact, the documents mention  presence of consuls around 1170 (See “Federico II e le Marche”, atti del convegno...["Frederick II and the Marches ", Conference Proceedings ...], Jesi, Palazzo della Signoria, 2-4 December 1994. p. 428). Tolentino was then subject to the Lordship of da Varano, Vicars of the Pope; apparently, already in 1260 Pope Alexander IV (1199 ca.-1261) had granted the vicariate to Gentile da Varano (died in 1294), but it is doubtful, because the actual granting of the vicariate was formally around 1355 with Papal Bull of Pope Urban V (1310-1360) in favour of Rodolfo II da Varano (died in 1384).

As early as the fourteenth century, the institution of "vicariate" in the territories under the rule of Church State was a way to legalize various lords, who had seized some cities often an act of force, while keeping them under the sovereignty and jurisdiction of the Pope. With the vicariate,  Pope did not have the "direct" domain of cities, but, while making many concessions to the Vicar ( collection of taxes,  possibility of appointing “Podestà”), he also safeguarded their power, because, first, Vicar could not sell or dispose of property or land; and, second, normally, the vicariate was an institution "fixed" (usually lasted three years); so much so that Tolentino then returned to the direct dominion of Church State, developing it, until the fifteenth century, especially with the enlargement of  walls. In the fifteenth century, indeed, Tolentino was considered one of the most important cities of Marches, especially for its crenellated walls, built in many forms, square, polygonal, round, according to the different strategies that were implemented to defend themselves from external attacks.

However, the fifteenth century was a very difficult period for Tolentino; the power of da Varano was thrown into crisis by the Sforza of Milan and city was involved in continuous wars among the great Soldiers of Fortune for its possession, as the Mauruzi, Piccinino, Bracci (Around the rule of Francesco Sforza in Tolentino and the continuing wars in which the city was involved in the fifteenth century see Giovanni Benadduci, "Della Signoria di Francesco Sforza nella Marca," Tolentino, 1892). Overall, under the papal rule, urban development, especially during the Renaissance, was modest, except for a strengthening of the walls built by Francesco Sforza (1401-1466), who commissioned the military engineer Giovanni Sodo (XV century), Ancona, considered a precursor of Sangallo (1445-1516) to build a new Fortress (G. Benadduci, pp. 132-133). G. Sodo had a reputation for being an excellent professional, so that  he was entrusted to the restructuring of  “Loggia dei Mercanti” of Ancona, built in 1443 (G. Benadduci, pp. 132-133, footnote 2).  A more symptomatic building impulse were recorded between the nineteenth and twentieth century, with the development of major industries such as leather processing, and even today Tolentino is a city with a significant industrial development and tourism-related activities for its artistic and archaeological heritage.