The Estonian Otepää is mostly known to the locals as a winter resort, but this is a place where known history stretches back into the early 12th century — in some form or another. Mostly this is due to the ever helpful neighbouring Rus states, the typical ones to try and extend into these lands being the Novgorodians. The Germans, of course, came in their own time and we know some about their adventures here as well, and for a while the city could have been called the capital of the bishopric in which it was based.
It is here where we can begin after a short note on the name of the place. Etymology is not always interesting, but at least in this case, with the Livonian writer Henricus Lettus mentioning this place as Caput Ursi — Head of a Bear.
The Southern Estonian landscape was shaped by glaciers in the last few glacial maxima, and it is due to these that this country is strongly undulating. A nicely defensible post was found by the tribes who came to these lands in the place we know as Otepää today. It is thought that the hill was fully surrounded by a lake at one point, but that the level has receded slowly and for the majority of the known period the fortifications have not had an accompanying moat.
The first concrete time we can place people here (insofar as a year is a concrete date) is in 1116 when Mstsislav of Novgorod conquered the place. In fact, much of the ensuing century, including the period of the German-led conquests, would be characterised by conflicting relations with the Novgorodians who no doubt retaliated as much as instigated these raids. In 1192, for example, the Novgorodians conquered the place again but left no lasting trail. Soon after this, the German period begins from which I will note some specific details but let the generic tone pass.
Namely, what is of interest is that the German-led forces started constructing a stone fortress on top of the hill in 1224, and this is what became the centre of the Bishopric of Dorpat for less than a decade until the administration was moved into Dorpat (now Tartu). Otepää remained an important centre of the fledgling state, however, and Hermann von Buxhoeveden kept control of it until deciding that a vassal would be more proper for taking care of the place. These vassals ended up being the often-recurring von Uexküll’s who managed to interfere in activities all around Terra Mariana.
The destruction of the castle — as it inevitably was destroyed, as war has swept across these lands many a time and left few survivors — came in the end of the 14th century. Another bishop deserving a mention, therefore, is Dietrich III Damerow who led the Bishopric into the war that saw it lose, if not land, then at least power. The opponent was the Livonian Order and the question was the degree to which the bishops in these lands, including the Archbishop of Riga, should be incorporated in the Order. Dietrich’s forces suffered defeat everywhere except at his capital of Tartu as his allies of Mecklenburg-Sweden and England were too far but the nearby Lithuanians agreed to a separate peace. Dietrich, humiliated and defeated, resigned a few years later, but the castle at Otepää was never restored.