Various hypotheses exist concerning the origin of the name Mons Galandrius. The greek term “gala” (milk) could refer to the grazing of sheep herds on the hill, and “gualdo” meant woods to the longobard tribes. But, most likely, the name originates from the “guala” or typical fishing net used on lake Trasimeno. 

The Castle's strategic position on the Tuscany-Umbria border has given it an important military role throughout the centuries, traced by several sources back to the Etruscans. Thus Perugia’s National Archeological Museum displays the famous “Montegualandro Stele” found on the hill. Subsequent Roman records indicate that Hannibal set up camp and part of his cavalry here before assaulting the troops of Consul Caio Flaminio in the historic battle of Trasimeno (217 B.C.). 

Charlemagne later donated the fortress to Ariberto, Lord of Monte Santa Maria, in 802 A.D. In 917 A.D. it belonged to the Marquis Uguccione II Bourbon and later, in 1165, Federico Barbarossa conquered it and gave it to the Ranieri family. Other manuscripts in the State Archives document the submission of Montegualandro on 29 May 1202 to the City of Perugia by the Marquises Uguccione and Guido Ranieri. 
In 1238 Pope Gregorio IX, vested the property rights of the Castle in Andrea di Giacomo Montemelino, Podestà of Perugia. The Montemelino family, of German origin, retained possession of Montegualandro till 1678 in spite of losing it several times by conquest. 

The Castle was destroyed on 13 March 1247 by Perugia because of Montemelino’s support and hospitality to Emperor Frederic II; the family was banished and the property confiscated. Pope Urbano IV then gave it back to the owners and signed a settlement with Perugia allowing the raising of toll fees by Montegualandro. 
In 1326 the Montemelinos, intending to sell the Castle, requested an estimate by the famous lawyer Cino da Pistoia. However, for the moment, the sale was not realised.
The Castle was conquered in 1334 by Piersaccone de Tarlati, Lord of Arezzo, in his fight with Perugia. 

From 1379 till 1383 the young Braccio Fortebraccio da Montone lived here with his mother Giacoma Montemelino. In 1383 her father, Tivieri, sold Montegualandro for 400 gold “fiorini” to the Casalis, Lords of Cortona, who continued to hold it thanks to Pope Bonifacio IX who officially signed it over to them in 1393. The Casalis held it until 1443 when Florentine forces conquered it and, in August of the same year, the Montemelinos retook possession of it. 
The fortress was thus greatly damaged and the Mayors of Perugia, knowing its importance, granted some funds to restore it to Nicolo and Francesco Montemelino. Unfortunately the following year Bernardino Fortebracci da Montone captured Montegualandro, but the Pope sent some troops who reconquered it, giving it back to Perugia. 

In 1517 the Castle was occupied by Giampaolo Baglioni, lord of Perugia, with his son Malatesta. The dispute was solved again by the Pope and Giampaolo Baglioni was beheaded in 1520 when Pope Leone X annexed Perugia to the Papal State. 
The Castle was then returned to the Montemelinos, who in 1544 obtained the Papal Delegate’s (Cardinal Crispo) recognition of Montegualandro county as a feudal property with its own jurisdiction and its own court and prison still identifiable to this day. 

In 1643 Ferdinando de’ Medici, Duke of Tuscany, occupied the Castle with his army, during the invasion of the “Stato Pontificio”. Then finally, in 1676, after Count Adriano Montemelino’s death, the whole county was sold “cum titulo” by Pope Innocenzo XI and bought, in 1678, by Ruggero Ranieri for 13000 “scudi”.
From this date Montegualandro follows the history of the Church States with its final fortress situated on the border of the “Granducato di Toscana”. For this reason a Customs office was established there. In 1798 after the French Revolution and the || proclamation of the Roman Republic, it became a fortress under the Trasimeno District and later (1809), under the same District, was controlled directly by the Napoleonic Empire. With the defeat of Napoleon in 1815, the Castle returned to the Pope who was to leave it in 1851 after the convention with the Granduchy of Tuscany. After the annexation of Perugia to the Italian Kingdom (1860) the “Montegualandro Azienda Agricola” was set up here and its wine and olive oil production became famous. 

Montegualandro Castle has thus defied the events of the centuries and can still be admired today, situated on its hill like a “falcon surveying its prey” as the poet Giosuè Carducci described it in 1877.