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The city of Ostashkov was first mentioned in the chronicle in 1371 under the name Klichen. It is located on a peninsula on the southern shore of Lake Seliger. For centuries, fishing has been the main occupation of local people. The appearance of the old town of the 19th century has been preserved on many streets of Ostashkov. 

The oldest part of the city of Ostashkov stretches from the Ascension Cathedral to the northern shore of the peninsula. Liberty Park and the small harbor are located on the site of the Trade Square of the Old Town of Ostashkov. In 1760, the Transfiguration Church was built on the square. The Bolsheviks destroyed it in 1928, but the bell tower of the church was preserved. Now it stands in the center of Liberty Park as an architectural monument of the 18th century. 

Stone and wooden buildings of the old Ostashkov have been preserved around the Liberty Park. Among them there is a small building of the City Folk Theater, built in 1892. The history of this theater began with a visit by residents of Ostashov to the home fortress theater in the Tolstoy estate on the west bank of Seliger. Now the Seliger Palace Hotel is located in this estate. After that, a theater was opened in Ostashov, and local residents were the artists there. 

Walking to the north, you will see the residential buildings of the old town of Ostashkov. A feature of 19th century houses in Ostashkov is mezzanines. Many houses need restoration, but in general the city looks authentic and beautiful. The city authorities are restoring old houses, making Ostashkov more attractive for tourists. A fire station building with a wooden tower, built in 1869, has been preserved near Liberty Park.  

In the northern part of the old town of Ostashkov is the Trinity Cathedral, built in 1685. Next to it is the Church of the Resurrection of Christ. Both temples have free-standing bell towers. The Ostashkov Museum of Local Lore is now open in the Trinity Cathedral. You can climb the bell tower of the cathedral to see the old town of Ostashkov from above.