Karkski Order Castle Ruins represent a significant medieval hill fortress in Viljandi County, originally established on the site of an ancient Estonian stronghold. Though a wooden stronghold existed at the location from at least 1248 during the Livonian Crusade, major stone construction commenced in the 13th century, with surviving structures dating to the 14th and 15th centuries. The fortress fell to Lithuanian forces in 1297–1298, and despite later rebuilding efforts, was ultimately destroyed during the Livonian War, becoming irreversibly ruined during the Great Northern War. Today, portions of the southwest side walls and sections near the moat remain visible, while the leaning tower of a Baroque church built within the ruins in the 1770s creates a striking architectural juxtaposition of medieval military and religious structures.