In prehistoric times, a large part of the present Vimperk region was covered in deep primeval forests. The history of human settlement starts as late as the Bronze Age, and is restricted mostly to the northern part of the area. The most important monument of that time that has been preserved to this day is the large prehistoric settlement of Věnec at Lčovice, which was still used by the Boii in the 1st century BC. In the Middle Ages, colonisation advanced slowly from the interior of Bohemia into the Šumava foothills, while the mountains of the Šumava were still hidden in the shade of the impenetrable frontier forest.
The first advances into the region coincide with the founding of Vimperk castle (before 1263) and are linked to the family of the lords of Janovice. The development was accelerated by a new branch of the famous Gold Trail, which led to a trading post under Vimperk castle from the turn of the 13th and 14th century. To protect the trail, the guardian castle Kunžvart was built close to the present border crossing at Strážný, followed in the 14th century by new settlements along the trail, bringing the population closer to the border of the country. The traffic along the Gold Trail steadily grew in intensity in the course of the 14th century, to the benefit of the whole region, and, of course, the lords in Vimperk. From the late 14th century and for centuries to come, these were the Kaplířs of Sulevice, whose rule was a true blessing; they led the region through the period of the Hussite wars and the following uneasy times of Jiří of Poděbrady, were able to resume the trade along the Gold Trail, and for their seat, Vimperk, they obtained the status of a town. They managed to successfully withstand the competition of the neighbouring town of Prachatice, the patron of the main branch of the Gold Trail, which was less than pleased with the existence of the Vimperk branch. In the 16th century both of the branches fell under the control of the Rosenbergs, under whose patronage the trade reached its peak.
The Thiry Years‘ War and the enforced monopoly of the Hapsburgs on the import of "their Austrian salt" into Bohemia via the town of České Budějovice meant the end of the glory days for the Gold Trail and a decline for the towns at its ends, as well as for the whole region. The salt trade along the trail eventually came to an end in the early 18th century, forcing Vimperk and the whole area to look for other livelihoods. This is reflected in the rise of glass-making, which provided jobs for the population, followed by other newly developing industries and printing works in Vimperk in the 19th century.
The population of Vimperk and the southern, mountainous part of the Šumava was exposed to Germanisation from as early as the 17th century, and this trend was continued under the new lords of Schwarzenberg (from 1719). The northern part of the region remained largely Czech, creating a bilingual situation in the area, which lasted until the end of WW II. The region suffered bitterly by the transfer of the German population after the war and the subsequent communist rule, but since 1989 it has been returning slowly to its original status – a prosperous link between Bohemia and the Danube basin in Germany, and an important centre on the Gold Trail.
The location of Vimperk on a rocky promontory above the river Volyňka, its picturesque skyline dominated by the castle, the fortifications, and the tall spire of the church of the Visitation of Our Lady, as well as a cluster of old houses below – all of this lends the town the air of the Middle Ages. For it was indeed the Middle Ages that originally brought the town into existence. The first inhabited site was that of the castle, founded originally as early as 1260 by King Přemysl Otakar II. The castle along with the estate later became a vassal or personal property of its burgrave Purkart of Janovice, King’s favourite and an important official of the kingdom. Before the end of the 13th century an early-Gothic church of St. Bartholomew was built near the castle. The lords of Janovice, fulfilling the will of the royal Přemysl dynasty, started colonisation of the uninhabited parts of the Šumava region to the south and east of Vimperk, and founded a settlement below the castle where merchants and craftsmen found new homes. From the turn of the 13th and 14th centuries, it became the target of caravans of pack animals coming along the new branch of the Gold Trail from Passau and bringing goods. Around the mid-14th century a parish church was added in the lower part of the settlement. In the second half of the 14th century Vimperk became royal property again, and King Václav IV entrusted it to the Kaplířs of Sulevice, who ruled there through the period of the Hussite wars and thereafter. Owing to their efforts the trade point below the castle was raised to the status of town in 1479 and encircled with fortifications of stone. The last member of the Kaplíř family in Vimperk, Peter, bequeathed the castle, the town, and the whole estate to a kin family of Malovec in 1494. They have, however, lost it after participating in an anti-Hapsburg rebellion in 1547, and were succeeded by a number of other foremost noble families of the Czech Kingdom – the lords of Hradec, the Rosenbergs, and the lords of Nové Hrady and Kolovraty. Vilém of Rosenberg grew particularly fond of Vimperk, and often stayed there along with his wives and train; to make the place suit his needs, he had the old castle rebuilt into a splendid chateau. His famous brother, Petr Vok of Rosenberg, was the owner of the chateau and the estate from 1565 to 1601, and a frequent visitor there, particularly in the 1560s. In 1630 Vimperk was bought by Duke Jan Oldřich of Eggenberg, becoming part of the vast Eggenberg dominion, and from 1719 of the Schwarzenberg dominion in South Bohemia.
A major source of money for Vimperk was the income from the trade on the Gold Trail. The trade in salt was extremely profitable and it is no wonder that it was the root of much controversy. Prachatice, the most important Czech town on the Gold Trail, perceived Vimperk as an unwanted rival, and took great pains to restrict its business activities, with varying degrees of success. Following an agreement in 1502, caravans could choose freely between Prachatice and Vimperk as targets for their loads of salt. The right to use the Gold Trail was even part of an old privilege granted to Vimperk by King Vladislav of Jagellon in 1479.
Vimperk was seized several times in its history: by the Hussites at the onset of the Hussite wars, then by the army of the Bishop of Passau fighting against Jiří of Poděbrady, and finally in 1619, at the beginning of the Thirty Years’ War by the soldiers of count Mansfeld. The decline of the town in the 18th century was followed by a period of new prosperity in the following century, when Vimperk became one of the few industrial centres in the Šumava foothills. By 1907 Vimperk had a glassworks producing hollow glass, two brickworks, lime works, machinery works, a boneware factory, a match factory, two sawmills, three printing works, two breweries, as well as a number of other smaller businesses. Vimperk remained an industrial town even after the transfer of the German population following WW II and throughout the communist period, however, since 1989 a number of enterprises have closed down. The new era means looking for a new identity, and Vimperk is set to build it on tourism.