Otepää is located the highest of the Estonian cities, up to 152 meters above sea level.

[1] The name Otepää means 'Ott's Head' in South Estonian, where ott is a euphemism for 'bear'.

Otepää (or Odenpäh) was historically important as the site of a Viking hill fort and medieval castle.

[3] The fortress was first mentioned in Rus' sources in 1116 when the princes of Novgorod and Pskov undertook an expedition against Tartu and Otepää.

The fort was attacked again in 1217, when Christianized southern Estonians stopped the Kievan Rus' advances.

[7] But it is more commonly believed that the castle was razed by the Livonian Order in 1396 during a conflict with the Bishopric of Dorpat.

[12] Otepää's municipal status was briefly restored in 1989 when the local government re-emerged in Estonia.