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The existence of numerous Etruscan-Roman settlements in this part of the country has been confirmed by archaeological finds consisting of necropoli and furnaces in the neighbourhood of Poggio all'Aglione, Bellafonte, Iano and Castelfalfi.
There is also evidence pertaining to the Paleo-Christian period in the crypt of the Oratory of S. Biagio (500 meters from Montaione).
After the barbarian invasion new settlements were built around the old ruins, especially in the places that offered most safety, such as Paterno, Marrante, Sala, and then in the Castle of Montaione, supplied as it was with numerous towers, and surrounded by solid walls.
The area came under the jurisdiction of the Longobard "Allone of Lucca" whose name must have been given to the Castle itself since it was mentioned in ancient documents as "Mons Allonis", then corrected to become "Montacone" as it is written in a document dated 988.
In 1118 the parish church dedicated to S. Regolo was built (2 km from the Porta Fiorentina) and remains a notable example of Romanesque architecture.
The town of Montaione was officially recognised in 1257, and then involved in the wars between San Gimignano, Volterra and San Miniato, though it gravitated mainly in Florence's orbit, submitting to the city's rule in 1369 and thence sharing its fate.
From 1200 on the art of glass-making was practised on the area. In the 18 th century an ordinance of the Grand Duke of Tuscany instructed masters glass-makers in Montaione to teach their art only to their fellow townsmen. Later the factories moved mainly into the Empolese area in the valley and the community became restricted to an agricultural economy.
The first time is remembered the Castle of Montaione is in a document of 981 with the name of "Montacunni" , even if we have detailed information from 1257 when it was in the territory of San Miniato.
In this period the hamlet was surrounded by solid walls with 11 towers, with a typical medieval shape that remember the roman's settlements with a central main road, a central square, lateral ways and two main doors: "Porta Grande or Fiorentina" and "Porta Piccina or Pisana", destroyed during the second world war.
In the centre of the village (today Piazza della Repubblica) there where a church, the Town Hall, and a bell tower with a big watch. The bell tower (remade in late 1700) and the Praetorian Palace dated back to XV century present on the façade many coat of arms of the aristocratic families of Montaione.
Walking in the central road of the historical centre is possible to see that still today shops present a window near the entrance door; a typical characteristic of the old workshop during XV century used as a shop-window or to let the light pass through.
In a document dated back to 1700 we can see the plan of the walled village with the two doors and 11 towers most of them have been the destroyed, but someone have been included in buildings like Palazzo Mannaioni.
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