It has been inhabited since prehistorical era, but grew up in
the Etruscan period from the 6th century B.C..
Castiglion Fiorentino takes place on the top of a high hill which separates the Valdichiana from
the Valtiberina. The first establishment, a village 240 roman feet long and 200 wide, appeared in this strategical point
and surrounded itself with walls.
Little by little, the village grew up; so did its walls, until the 4th century B.C., in
which it reached the site they kept on having up to the medieval era, and that they still have nowadays, excepted the
northern end, which did not include its most external part, that it got in the 14th century.
It also structures itself, with a street network drawn around the 2nd century B.C.,
following the level curves that inevitably rule the town planning of a hill. You can imagine the ancient town’s borders
walking through the Corso Italia and the Via San Michele, which were the main streets, what they still are, despite of
the nibbling of these borders by the expansion of the town.
The Roman conquest brought the agricultural products with the villae.
The name of Castiglion appeared in the 10th century. The formation of the village
begun in the second half of the 12th century. In 1289, Castiglion went under Florence's domination,
then, in 1303, it went back under Arezzo's domination and was named Castiglion Aretino. In 1344, conquested by
Perugia, it became Castiglion Perugino. Finally, in 1384, it went back under Florence's domination and took back
its former name of Castiglion Fiorentino.
In 1765, the Valdichiana was improved, which allowed a demographical and economical
In 1744, Castiglion Fiorentino annexed the villages of Montecchio, Mammi and Montanina.
Between 1800 and 1814, Napoleon's troops ruled the town.
During the Second world War, the whole town suffered important damages.