Between the 13th and 15th centuries, the Pskov Republic was engaged in border conflicts with the Livonian Order, Archbishopric of Riga and the Great Duchy of Lithuania.

[4] The inhabitants of the Kokshiono parish, however, requested the veche (council) and the Prince of Pskov to secure the border through military means to save them from Livonian raids.

In 1476 a wooden fortress was founded on the Lada river by two posadniks of Pskov – Alexey Vassilievich and Moisey Fyodorovich.

The town was ruled by the vicegerent appointed from Pskov and was an administrative center of the county consisting of eight parishes: Borisoglebskaya, Grivskaya, Kokshinskaya, Lebetskaya, Korovskaya Ovsitskaya, Yolkinskaya and Kukhovskaya.

[12] In 1581 Polonian units led by King Stephen Báthory passed through Vyshdorodok to besiege Pskov.

After the Bolshevik Government failed to finalize the Treaty of Brest-Litovsk with the Central Powers, the latter resumed their advance eastwards on Pskov and Petrograd, resulting in the village coming under German control.

Shortly after the October Revolution, the Soviets seized control over most of the Pskovian municipalities, including Vyshgorodok.

[16] In January 1920 Vyshgorodok was attacked by advancing Latvian republican units and the frontline as of noon 1 February 1920 was stipulated as the border demarcation line by the Latvian–Soviet Peace Treaty between the Latvian Republic and Russian Soviet Federative Socialist Republic, which left Vyshgorodok with Latvia.

In 1925 it was renamed Augšpils (a Latvian translation of the original name) and made part of Pytalovo (1925–1938 Jaunlatgale, 1938–1944 Abrene) county which also contained other territories of the Pskov Governorate annexed to Latvia by the Treaty of 1920.

From July 1941 until June 1944, Vyshgorodok was part of the Nazi occupation zone covered by the Reichskommissariat Ostland, Generalbezirk Lettland, Gebietskommissariat Dünaburg.

Latvian and Estonian peasantry with no means to buy enough land from their landlords were forced to seek cheaper options available right across the Eastern border of the Governorate of Livonia.

[21] According to the 1911 statistical reference book for the Ostrov county of the Pskov Governorate, Vysgorodok parish accommodated 1,800 immigrants who either purchased (pustoshniki) or leased plots of land, 300 of whom were from Livonia and Estonia.

«Об установлении границ и статусе вновь образуемых муниципальных образований на территории Псковской области», в ред.