The castle was probably built in the 13th century most likely in place of an ancient Estonian stronghold. The bailiwick of Karksi was first mentioned in 1248. The stronghold had a chapel dedicated to Apostle Peter. The first reference was made to a local clergyman in 1298. The present stone church, very simple in design, was built in the same place between 1773 and 1778. St. Peter’s Church is in the ruins of Karksi castle. The tower of the church is leaning, the inclination of the tower’s top is 205 cm at the moment. In 1994 it was decided to save the tower using complicated "construction surgery" developed while stabilizing structures in the old town of Tartu. Eight 10- metre-tall bored piles along with concrete beams penetrating foundations form a new bearing surface for the tower. As a result, the further leaning of the tower has stopped.
On the way which takes you to the stronghold, in the former cemetery of the Knights of the Order of the Sword, stands a nice Baroque chapel among trees, built in the early 18th century by Field Marshal George Reinhold von Lieven, the owner of the Karksi manorial estate. The coats of arms of the Lievens and the Mannteuffels have been fixed to the chapel doors. The chapel, similarly, was built with one side on the former foundation and therefore is somewhat leaning. The buildings of the Karksi manor have perished.
German crusaders known as the Livonian Brothers of the Sword began construction of the Cēsis castle (Wenden) near the hill fort in 1209. When the castle was enlarged and fortified, it served as the residence for the Order's Master from 1237 till 1561, with periodic interruptions. Its ruins are some of the most majestic castle ruins in the Baltic states. Once the most important castle of the Livonian Order, it was the official residence for the masters of the order.
In 1577, during the Livonian War, the garrison destroyed the castle to prevent it from falling into the control of Ivan the Terrible, who was decisively defeated in the Battle of Wenden (1578).
In 1598 it was incorporated into the Polish-Lithuanian Commonwealth and Wenden Voivodship was created here. In 1620 Wenden was conquered by Sweden. It was rebuilt afterwards, but was destroyed again in 1703 during the Great Northern War by the Russian army and left in a ruined state. Already from the end of the 16th century, the premises of the Order's castle were adjusted to the requirements of the Cēsis Castle estate. When in 1777 the Cēsis Castle estate was obtained by Count Carl Sievers, he had his new residence house built on the site of the eastern block of the castle, joining its end wall with the fortification tower.
Since 1949, the Cēsis History Museum has been located in this New Castle of the Cēsis Castle estate. The front yard of the New Castle is enclosed by a granary and a stable-coach house, which now houses the Exhibition Hall of the Museum. Beside the granary there is the oldest brewery in Latvia, Cēsu alus darītava, which was built in 1878 during the later Count Sievers' time, but its origins date back to the period of the Livonian Order. Further on, the Cēsis Castle park is situated, which was laid out in 1812. The park has the romantic characteristic of that time, with its winding footpaths, exotic plants, and the waters of the pond reflecting the castle's ruins. Nowadays also one of the towers is open for tourists.