Derbent vs Madison

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Derbent (Russian: Дербе́нт; Persian: دربند‎; Lezgian: Кьвевар, Цал; Azerbaijani: Dərbənd; Avar: Дербенд), formerly romanized as Derbend, is a city in the Republic of Dagestan, Russia, located on the Caspian Sea. It is the southernmost city in Russia, and it is the second-most important city of Dagestan. Population: 119,200 (2010 Census); 101,031 (2002 Census); 78,371 (1989 Census).Derbent occupies the narrow gateway between the Caspian Sea and the Caucasus Mountains connecting the Eurasian Steppe to the north and the Iranian Plateau to the south.

Derbent claims to be the oldest city in Russia with historical documentation dating to the 8th century BCE, making it one of the oldest continuously inhabited cities in the World. Due to its strategic location, over the course of history, the city changed ownership many times, particularly among the Persian, Arab, Mongol, Timurid, Shirvan and Iranian kingdoms. In the 19th century, the city passed from Iranian into Russian hands by the Treaty of Gulistan of 1813.

Source: Wikipedia