Ivaylovgrad is a town in Haskovo Province in the very south-east of Bulgaria set near the river Arda in the easternmost part of the Rhodope Mountains. It is the administrative centre of the homonymous Ivaylovgrad Municipality. As of December 2009, the town has a population of 3,756 inhabitants.
Byzantine eparchial lists from the time of the 9th-10th century mention a bishop’s centre by the name of Lyutitsa on the site of present-day Ivaylovgrad. According to John VI Kantakouzenos (1347–1354), his infantry reached the fortress in 1342–1343. The settlement was destroyed by the Ottoman Turks during their invasion of the Balkans in the 14th-15th century.

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