The history of La Flèche encompasses ancient and more recent events, with a particularly notable increase in occurrence in the modern era. Despite evidence of human habitation dating back to prehistoric, La Flèche was established relatively recently, around the year 1000. This period saw the construction of a fortress along the banks of the Loir, which would become a defining feature of the city's landscape. Its strategic location on a navigable waterway and at the crossroads of routes linking France's major western provinces resulted in its ownership by the Plantagenets, counts of Anjou, and kings of England, for some time. However, La Flèche was largely overlooked by its various lords at the end of the Middle Ages until Françoise d'Alençon retired there at the end of her life in 1537.

At the turn of the 17th century, La Flèche experienced a renewed surge in growth and prosperity, largely due to the favor and patronage of Henry IV, King of France, and Guillaume Fouquet de La Varenne. Under Fouquet's stewardship as the city's governor, La Flèche underwent significant modernization and emerged as a prominent administrative and judicial center. However, it was primarily the establishment of the Jesuit college in 1603 that marked the beginning of a period of great prosperity. One of its former students, Jérôme Le Royer de La Dauversière, played an important role in the spiritual renewal of La Flèche while also being one of the founders of the city of Montreal in Canada. In 1641 and then in 1653, hundreds of residents from La Flèche committed to founding a colony there.

La Flèche was marked by the passage of the Vendéens on two occasions during the Virée de Galerne in 1793. Following this, the area underwent a new development period when Napoleon I established the Prytanée National Military Academy there in 1808, utilizing the premises of the former college. The town was subsequently occupied by Prussian forces in 1815 and again in 1871. During the First World War, La Flèche suffered significant losses, with 339 of its residents killed.

Following the Second World War, La Flèche experienced a period of expansion through the annexation of two additional communes, while simultaneously maintaining a trajectory of economic growth. The conclusion of the 20th century saw the initiation of several substantial urban developments, including the expansion of the municipal administration building, the establishment of a bus station, and the refurbishment of the town center. These initiatives persisted into the 21st century with the construction of a recreational facility, a comprehensive sports complex, a new cinema, and the restoration of the facades.

Occupation of the territory from Prehistory to the Early Middle Ages

The archaeological record indicates that human occupation in La Flèche and its surrounding area dates back to the Neolithic period. This is evidenced by the discovery of numerous artifacts from this era, as well as several megaliths in the Loir Valley. Among the discoveries were Campignian stone tools found near the area known as La Vallée, located to the north of the city. Another notable find is the menhir, or standing stone, called La Roche Voyer, which is situated within the commune, near the former Mélinais Abbey. Despite these early indications of human activity, the region saw sparse settlement during this period. The town's development occurred much later, with only one trace of occupation during antiquity: a Gallo-Roman villa, or substantial farmhouse, on the site of the present-day Saint-Jacques district.

During this period, Cré, rather than La Flèche, served as a crucial relay station for the cursus publicus, the Roman postal service, along the Roman road connecting Le Mans and Angers. Situated on the Champs Priory site, Cré provided a crossing point for the Loir via a ford. The occupation of Cré spanned a more extended period and was uninterrupted, with evidence of prehistoric settlement in the form of approximately fifteen Neolithic tools and indications of early Romanization, including the discovery of a Venus statuette, pottery shards, and Roman coins. Cré retained its significance through the Carolingian era, becoming the principal settlement of a condita (an administrative district) within a pagus (a county-like area) and serving as the site of a mint in the seventh century.

Meanwhile, in La Flèche, the Gallo-Roman villa underwent a gradual transformation into a medieval village, with the establishment of a church on the site of the present-day Notre-Dame-des-Vertus chapel. The early settlement of other peripheral areas of La Flèche has also been evidenced by the discovery, before World War II and again in 1990, of a set of thirteen Merovingian sarcophagi situated near the Grand-Ruigné hillside.

From the founding of the city to the end of the Middle Ages La Flèche was established shortly after the year 1000 and rapidly acquired a prominent position. In 1051, Jean de Beaugency, the younger son of Lancelin I, the lord of Beaugency, and Paula du Maine, the youngest daughter of Count Herbert I Wake-Dog, sought a location in which to construct a castle within his domain of Fissa (fiscal land). He selected the area for his fortress, which was constructed on stilts, by fortifying several islands in the Loir at the site of the current . Additionally, he built a bridge to redirect a portion of the commercial traffic from the medieval route connecting Blois to Angers, necessitating the payment of a toll by merchants utilizing the route. For this reason, Jean de Beaugency is regarded as the inaugural lord of La Flèche. The site rapidly acquired both strategic and commercial significance, situated on a navigable waterway and at the confluence of routes from Paris to Anjou and from Brittany to Touraine. Moreover, Jean de Beaugency's position as a vassal to the Count of Anjou but related to the Counts of Maine through both his mother and his wife placed his territory at the center of disputes between the two counties. In 1067, the army of La Flèche was referenced in the Chronicle of Saint-Aubin.

In 1078, the town was besieged by the forces of Fulk IV, Count of Anjou, who was supported by Duke Hoël II of Brittany. Their objective was to oppose Jean de Beaugency's alliance with the Normans, who were considered enemies of the Anjou counts. William the Conqueror, King of England and Duke of Normandy, became involved in the conflict to defend his ally. However, open combat was averted through the intervention of several clergy members, including Bishop Odo of Bayeux, who facilitated a mediation process. The peace treaty was eventually concluded in an area near La Flèche, known as Blanche-Lande or Lande de la Bruère.The land in question is situated within the boundaries of the Thorée-les-Pins municipality. This provisional cessation of hostilities did not fully reconcile the lord of La Flèche with Fulk IV of Anjou. In 1081 or 1087, the fortress was captured and burned. In that same year, Jean de Beaugency donated the chapel of his castle to the Benedictine monks of Saint-Aubin Abbey in Angers, as well as the , located farther east in the neighboring parish of Sainte-Colombe. His third son, Elias of La Flèche, succeeded him and became the first lord to bear the town's name. However, like most lords of that period, he only resided in the area a few days per year, as he moved between his various estates. The town's management and administration were delegated to seneschals, a role held by the Cleers family at La Flèche around the 12th century, for both Elias and his successors.

In 1093, Elias of La Flèche procured the county of Maine from his cousin Hugh V of Este. Additionally, he facilitated the town's expansion through the establishment of the in 1109, which was entrusted to the Benedictine monks of Saint-Aubin Abbey in Angers. Upon his demise, he bequeathed only a daughter, Erembourg, who married Fulk V of Anjou, son of Fulk the Fat and future King of Jerusalem, circa 1110. This union definitively merged Maine with Anjou, including the seigneury of La Flèche. From that point onward, La Flèche remained under the control of the Plantagenet counts of Anjou, who also held the title of King of England. The town continued to flourish with the establishment of several religious institutions, including the Saint-André Priory, which was founded in 1171 by monks from Saint-Mesmin Abbey in Orléans. The monks were granted land by Henry II Plantagenet. In 1180, Henry II, King of England, established Saint-Jean Abbey of Mélinais in the forest of the same name, located to the southeast of the town. By the end of the 12th century, the seigneury of La Flèche had passed to the Beaumont family, through . However, the circumstances surrounding this succession remain unclear.

In 1224, La Flèche was elevated to the status of archpriesthood. In 1230, a few years later, King Louis IX of France stayed in La Flèche for two days while French troops, under orders from regent Blanche of Castile, marched on Brittany with the objective of ending the alliance between Duke Peter I and Henry III of England. Notably, Louis paid homage to the statue of Notre-Dame-du-Chef-du-Pont in the chapel of the same name, which is located at the entrance to the Carmes bridge over the Loir and adjoins the . This modest, transept-less edifice had also been visited by Thomas Becket nearly a century earlier and remained a significant pilgrimage site in the region. At the beginning of the 15th century, the clergy of organized a procession there during the Notre-Dame festivals.

In 1386, during the Hundred Years' War, the English besieged and burned La Flèche Castle. The fortress was occupied by the English until 1418, during which time it was besieged on numerous occasions.

In 1431, a dispute arose between John II, Duke of Alençon, and his uncle, the Duke of Brittany, concerning the dowry of Mary of Brittany, the latter's mother. The matter in question pertained to the lack of a fully settled agreement regarding the aforementioned dowry. Subsequently, John II had the chancellor of the Duke of Brittany, Jean de Malestroit, arrested and held him prisoner at the Château de La Flèche and then at that of Pouancé. In the subsequent years, the territory of La Flèche was elevated to the status of a barony. On September 10, 1453, John II of Alençon, the lord of the region, made a declaration to René of Anjou, outlining its various titles, rents, and properties. His son, René of Alençon, established a Third Order Franciscan monastery in the area in 1484, followed by a Cordeliers convent four years later.

Modern era

The Château-Neuf of Françoise d'Alençon

Until the mid-16th century, La Flèche was a city that was largely ignored by its lords, who rarely or never resided there. Local historian Charles de Montzey characterized the city as "shrouded in obscurity" and "open to all comers." Following the death of her husband in 1537, Françoise d'Alençon elected to take up residence in this lordship, which she had inherited from her parents and received as part of her dowry from her husband, Charles IV of Bourbon. At that time, the feudal Château de La Flèche, constructed on the Loir, was in a state of advanced deterioration and lacked comforts. Françoise d'Alençon transferred it to the religious congregation of the Carmelites (from which it derives its current name) and initiated the construction of a new residence, the Château-Neuf, situated at the location of the present Prytanée National Military, slightly north of the original castle, beyond the city walls. The architectural design was assigned to the renowned Jean Delespine, who oversaw its construction between 1539 and 1541.