Pytalovo (the alternative name of which was Novo-Dmitrovskoye) was known as a village in Vyshgorodok volost, Ostrovsky Uyezd, Pskov Governorate since the end of the 18th century. In the course of World War I, in February 1918 the German Army advances on Pskov and Petrograd capturing western part of Pskov Governorate until November when the Red Army retakes it. In May 1919 г. advancing pro-czarist Russian North-Western Army of Gen. Nikolai Yudenich supported by Estonian and Latvian republican units recaptures westernmost part of the Pskov Governorate.