The name of Montelupone began to appear in documents dated back to the mid-12th century, and the medieval urban structure confirms the origins in that historical period.
From 1926, the discoveries of a necropolis dating from the sixth century b.C., earthen vessels, amphorae, stone arrowheads, shards of brick and a Roman furnace confirm that the territory was inhabited before the birth of the municipality.
Montelupone’s “Castle” castrum dates back to the XI-XII centuries, within what was the territory of Marca Anconitana. From archival documents we know that in 1224 the city had its consuls, then in the 13th century it had already an established existence even though until the fifteenth century it saw passing into the territory soldiers of fortune, powerful lords, fighting leaders of adverse factions: Guelphs and Ghibellines. In the territory the Bishop of Fermo sovereignty ended in 1586 after he was elected Pope, in 1585, Pope Sixtus V. Montelupone became part of the new diocese of Loreto. In the seventeenth and eighteenth century it became the Government of municipalities, the middle class of Marca made of nobles who had exclusive charges, offices and magistracies and who were distinguished in society by the standard of living and dwelling, usually two or three storey buildings with several rooms used as representative places. Emerging families were Tomassini-Barbarossa, Basvecchi, Celsi, Eleuteri, Garulli and others, each one with her own palace.

In 1799 Montelupone hosted part of the Leopardi’s Recanati family, fleeing the city because of the brigands who infested it after the passage of French troops.

After the Congress of Vienna, in 1817 the town participated in the revolutionary attempt Marche-Romagna, it was one of the first outbreak of the Carboneria, with a series of secret meetings that took place in Basvecchi Palace (then Emiliani). The revolt had to take place in Macerata during the night between the 24 and the 25 August 1817 but it was suppressed in the beginning and the rioters were arrested.
In 1860 in Montelupone stopped the French troops of General Lemorciere and De Pimodan to stop the advance of the troops of the Piemontese General Cialdini, before moving to Castelfidardo’s defeat that marked the annexation of Marche to the Kingdom of Sardinia, and then the unification of Italy.
In World War II, the country was occupied by German troops, which hit Saint Chiara’s church during the retreat, after the advance of the Polish and British allies.

The historic centre of Montelupone, intact in its medieval aspect, is enclosed by a well preserved walls and four gates.

The country was built in stages starting from a central nucleus, located in the highest part of the hill, with extensions called “onion icing” that adapt to the altimetry of the places proposing the trend gradually expanded from the vertex to the base.
The walls go along the entire perimeter of the Center, for about 1000 meters in length, although there are some huddled houses in certain points. In some places the towers are situated, made of two different types: square or shaped strut. The latter type built in the 15th century, testifies the Malatesta domination, preserves in its sides two similar bombers to those present in the towers of the castles of Gradara and s. Arcangelo di Romagna made erected by Sigismondo Pandolfo Malatesta

There are four gates:

PORTA S. STEFANO also called Porta Marina because facing the sea, or Porta delle Grazie or delle Fontanelle. It dates back to the 14th century but it has undergone several renovations, including the most important of 1804. It was rebuilt in brick with beautiful frames and terracotta spire motifs and a Ghibelline shaped battlements. Inside, in the upper part a passage was built in the early ‘ 900 linking the two private buildings adjacent to it: palazzo Emiliani with palazzo Ricci.

PORTA ULPIANA also referred as S. Michele (Roman name, derives from the Emperor Marcus Ulpius Traianus). The original structure from the 14th century was angular and we can note it on the external side by a walled opening. It’s the most interestin door from an historical and architectural point of view.
Also the fifteenth-century ravelin is very interesting, an indipendent pentagonal fortification, protruding from the perimeter of the walls and built to protect a door, perhaps erged in Montelupone under the Malatesta fortress, of which the great arch is still visible. In the Baroque period a gate was added for decorative purposes, the one we see today. Opposite, in the clearing now used for parking, between ‘ 800 and ‘ 900 it was the clearing of the athletic field where they played at “pallone col bracciale”.
Famous was the team of Montelupone that repeatedly challenged Treia in Macerata’s “Sferisterio”.

PORTA DEL CASSERO also called Porta Castello. It dates back to the Medieval period. It’s the door located at the highest point and refers to the first walled core walled in the Cassero’s fortress. Renovated in 1500 then rebuilt in 1861 it presents one semicircular arch terminating at the top with a slightly projecting entablature decorated with geometric shapes.

PORTA DEL TREBBIO also called Bubiano or Ubbiano gate. It dates back to the Medieval period and it’s located at the intersection of an ancient road junction with mount Bubiano (San Nicolò) and the San Firmano’s monastery.

ROCELLINO is an embattled watchtower towards the Valley of the Potenza river, rest of the ancient Cassero, that is the most elevated part of the fortress.

THE “PALAZZO DEL PODESTÀ” AND THE CIVIC TOWER
The “Palazzo del Podestà” or “dei Priori” is the oldest and largest architectural survey of the square and the historic center of Montelupone. The building dates back to the late 13th and the early 14th century and it was an artwork of Lombard masters. The façade, whose low horizontal body contrasts with the crenellated Tower, high, adjacent to the building is compared to similar structures that are located in the municipality of Montecassiano and Offida. The current building shows five openings on the ground floor that make up the portico resting on stubby pillars circular/octagonal, upstairs there are five lancet windows, identical, resting on a slightly projecting frame. The building is the result of two separate buildings: the oldest one adjacent to the Tower, the other body adjacent to the Church of the Pietà annexed to the convent of the Poor Clares is back to the 14th century. The redevelopment and restoration of the portico and of the building were carried out between the end of 800 and the beginning of ‘ 900. Inside, the halls of the first floor host the City Museum of Montelupone.

The City Tower was built, at his own expense, in the 14th century as it’s indicated in a coat of arms, carved on a stone built into the wall towards the base, under the Clock Tower, put in that toward at the end of the 16th century, probably in 1510 when renovations were carried out at the top, at the Crown. Following the annexation of the municipality of Montelupone to the Diocese of Loreto, it was placed in the Tower a coat of arms of Pope Sixtus V, in travertine. It was never castellana, that is of the local accounts, but only municipal. At the beginning it was a Guelph crenellations, to demonstrate the power of the Holy Office on the region, until 1844 when it was decided to superimpose the rectangular and plates battlements with a truncated pyramid shape pinnacles, to solve the problem of water infiltration. Other interventions were made in 1896 and in particular where the stability of the structure was damaged by the big bell chimes and after the second world war.
Built entirely of bricks, it’s 25 metres high and divided into six shelves, including the underground and the terrace. Along the four walls several windows open in each shelf and four large bell gallery.

The town hall overlooking the main square was built during the Napoleonic Kingdom of Italy (1807-1814) on the spot where a building existed in medieval style, reserved for residential use of the Lords of the village and residence hall. During the 19th century it underwent several restorations and the current city hall building is the result of elaboration of projects of different architects. The property, in one body, in neo-classical style, has on the ground floor a porch punctuated by five arches resting on pillars, on the first floor there are five windows divided by pilasters.
Inside of considerable importance there is the municipal theatre of considerable importance, named Teatro degli Angeli  (in honor of the original Angeli’s family of Montelupone, which boasted members in the literary and legal fields -the most well-known Nicola degli Angeli Secretary of Pope Sixtus V of Marche-).
In 1869, the architect Ireneo Aleandri (designer of the Sferisterio’s arena in Macerata) presented to the City Council a project, but remained only on paper. Instead it was built from 1884 to 1888 under the project presented by the architect Giuseppe Sabbatini. The horse-shaped hall with two tiers of columns and thirteen stages and a crown forming the balustraded gallery. The classical forms have an evident Palladian influence. The decorations and the ascolani paintings were entrusted to John Pike and Domenico Ferri (Royal palaces decorator). It has accessed through the entrance of the town hall.