The earliest mention of Pskov in any chronicle dates to 903, when a record describes the marriage of Igor of Kiev to a local woman named Olga — later canonized as Saint Olga of Kiev, the first ruler of Rus to convert to Christianity. Pskovians sometimes count this as the founding date, and in 2003 a great jubilee marked the city's 1,100th anniversary. The original name was Pleskov — "the town of purling waters" — for the Velikaya River and the smaller Pskova that joins it at the foot of the kremlin. In English the city was once known as Plescow. In 1241 the Teutonic Knights took the city. Several months later Alexander Nevsky took it back, in a campaign Eisenstein dramatized seven centuries later. To secure independence from the German knights, the Pskovians elected a Lithuanian prince named Daumantas — known in Russia as Dovmont — as their military leader in 1266. He built the inner fortifications still called "Dovmont's town" today, and his sword and remains are preserved in the kremlin.

From 1348 until 1510, Pskov was an independent republic governed by an assembly of citizens. Its law code, the Pskov Charter, was one of the principal sources of the all-Russian code that Ivan III issued in 1497. German merchants had a presence in the city from at least the 13th century, and the Hanseatic League maintained a trading post here in the early 16th century. Then in 1510 Vasili III of Moscow simply occupied Pskov. He deported three hundred families to central Russia to break the power of the local elite. The deportation became the subject of an opera by Rimsky-Korsakov in 1872. Pskov stayed in Moscow's hands but kept fighting for its life. In 1581-1582, during the final stage of the Livonian War, a Polish-Lithuanian army of 50,000 men under King Stephen Báthory besieged the city. The Polish king mounted thirty-one attacks. The defenders, mostly civilians, repelled every one — even after one of the city walls was breached, they filled the gap and held. The Swedish siege of 1615 ended the same way, and led to the Treaty of Stolbovo.

Peter the Great's conquest of Estonia and Livonia in the early 18th century pushed Russia's border west and ended Pskov's role as a frontier fortress. The city became a quiet provincial capital. In 1897 it was 80% Russian by mother tongue, with substantial Jewish, German, Latvian, and Estonian minorities. World War I made it briefly central again. Pskov became headquarters for Russia's Northern Front, and on 15 March 1917 Tsar Nicholas II abdicated aboard the Imperial Train at the city station, ending the Romanov dynasty. After the Brest-Litovsk peace conference of 1917-1918, the German Army occupied the area. Then between May and August 1919, during the Estonian War of Independence, Estonian forces held the city under a White Russian commander named Stanisław Bułak-Bałachowicz, who put an end to press censorship and helped restart the war-impoverished economy.

The medieval citadel that had withstood Polish kings did not stand against Wehrmacht artillery. German forces occupied Pskov from 9 July 1941 until 23 July 1944. They operated a forced labor camp in the city for Jewish men and women — most of whom did not survive the occupation. In February 1944, as Soviet forces drove west, Russian bombing killed thousands of people in the still-occupied city. A huge portion of the pre-war population was dead by the end of the war. Pskov has struggled ever since to regain its position as a major regional center. Yet so much survived. The Pskov Kremlin still stands, with the 256-foot Trinity Cathedral founded in 1138 and rebuilt in the 1690s rising inside its walls. Around the city there are several dozen small white churches, mostly from the 15th and 16th centuries — the picturesque local style that UNESCO recognized as a World Heritage Site in 2019. The 17th-century merchant mansions like the Pogankin Palace and the Salt House preserve civil architecture that almost nowhere else in Russia kept intact. Pskov never quite recovered, and exactly that gives it its character.