The first reliable mentioning of Ashmyany (in the Lithuanian Chronicles) tells that after the death of Gediminas in 1341 the town was inherited, among other places, by Jaunutis. In 1384, the Teutonic Knights attempted to attack A�miany as a beginning attempt to destroy the hereditary state of Jogaila. The Teutons managed to destroy the town, but it quickly recovered. In 1402 another Teutonic attack on the city occurred, but was bloodily repelled and the Teutons were forced to withdraw to Medininkai.
In 1413 the town became one of the most notable centres of trade and commerce within the Vilnius Voivodship. Because of that, in 1432 it became a battlefield of an important battle between the royal forces of Jogaila under �ygimantas K?stutaitis and the forces of �vitrigaila allied with the Teutonic Order. After the town was taken by the royalists, it became a private property of the Grand Dukes of Lithuania and started to develop rapidly. However, less than a century later the town was yet again destroyed and burnt to the ground, this time by the forces of Muscovy in 1519. The recovery did not occur as quickly as the previous time and in 1537 the town was granted with several royal privileges to facilitate the reconstruction. In 1566 the town finally received a city charter based on the Magdeburg Law, which was later confirmed (along with the privileges for the local merchants and burghers) by king Jan III Sobieski in 1683. In 16th century the town also became one of the most notable centres of Calvinism in the Polish-Lithuanian Commonwealth, after Miko?aj "the Red" Radziwi?? founded a collegiate and a church there.
In 1792 king Stanis?aw August Poniatowski confirmed all the previous privileges and the fact, that the town of Oszmiany, as it was called back then, was a free city, subordinate only to the king and the local city council. It was also then that the town received the first Coat of Arms in its history. Composed of three fields parted per pale,
