Welcome to Otepää, a town with over 900 years of history—a place where history, sports, and culture have intertwined for centuries. Otepää’s historical significance was first documented on March 9, 1116, during ancient Estonian times. Evidence of human activity in the area dates back to the 6th century BCE, with continuous settlement since the 6th–7th centuries CE. Despite numerous invasions, the resilience and determination of Otepää's inhabitants have endured through the ages.

• Ugandi was a historical county in southeastern Estonia over 900 years ago, with Otepää as its main center.
• The Ugala Theatre, founded in Viljandi in 1920, was named after Ugandi. 
• The Latvian name for Estonia, Igaunija, originates from Ugandi.

The Otepää Hill Fort, located just a few hundred meters from Ugandi Resto, has a long and distinguished history. For over half a millennium, it served as a fortress for ancient Estonians, followed by nearly two centuries as a stone castle built in 1224.

In the early 12th century, Otepää was one of southeastern Estonia’s most significant centers. By the end of the ancient era, in the first quarter of the 13th century, Otepää had become the main power center of the Ugandi county. If history had taken a different course, Otepää might have even surpassed Tartu in importance today.

The historic hill fort gave Otepää its name, as the fortress on the site resembled the shape of a bear's head (in Estonian, "oti" = bear, "pää" = head). The Otepää fortress is mentioned in Henry of Livonia's Chronicle as Odenpe and Odempe, meaning “bear’s head.” Similarly, Russian chronicles refer to it as Медвежья голова (“bear’s head”).

The first written mention of Otepää dates back to 1116, during a military campaign led by the Prince of Novgorod. This campaign was considered a significant event across the territory of Kievan Rus.

The 1116 expedition did not seem to leave any lasting consequences for the inhabitants of Otepää. There is no evidence that the people of Otepää were subsequently required to pay tribute to the princes of Novgorod. The fortress was rebuilt and fortified. Despite these efforts, the fort was repeatedly looted, burned, and reconstructed over the following decades.

In 1192, troops of Prince Yaroslav Vladimirovich of Novgorod burned the fortress during a raid. According to Henry of Livonia's Chronicle, the fortress was set ablaze again in 1208 by the combined forces of the Bishop of Riga, the Livonian Brothers of the Sword, and Tālava Latgalians and Livonians. Two years later, the fort was besieged by the princes of Novgorod and Pskov, leading the defenders to agree to pay a ransom. Later that year, Riga's forces returned, capturing and burning the fortress once more.

At the beginning of 1223, an anti-Order uprising broke out in Ugandi, during which the knights of the Order and other Germans in Otepää were killed or captured. After the suppression of the rebellion, Ugandi came under the control of the Bishop of Tartu, who ordered the construction of a new stone fortress on the site of the old one. At that time, Otepää served as the center of the bishopric.

During the St. George’s Night Uprising in 1343, the bishop’s forces, led by Johan Üxküll, used Otepää as their headquarters. However, in 1396, the Order destroyed the Otepää bishop’s castle, and it was never rebuilt.

With the establishment of the Bishopric of Tartu, the name Ugandi quickly fell out of use and was no longer referenced. In 1928, there was consideration to rename Tartu or Võrumaa as Ugandi. The matter was referred to the University of Tartu by the parliament’s leadership, but the university’s representatives did not support the idea, and it remained just a proposal.

Otepää is the birthplace of the Estonian national flag. The first blue-black-and-white flag was ceremonially consecrated on the evening of June 4, 1884, in the hall of the Otepää parsonage. However, this consecration did not yet grant the flag public recognition or the right to be displayed. The flag was hidden in the apartment of the Estonian Students' Society (EÜS) in Tartu, awaiting its time.

On February 24, 1918, the first foundational document of independence, the "Manifesto to the Peoples of Estonia," was proclaimed under the fluttering blue-black-and-white flags. Shortly afterward, the German occupation temporarily suppressed these colors, but on November 21, 1918, the Provisional Government of the Republic of Estonia officially recognized the blue-black-and-white flag as the national flag of Estonia.

Through the centuries, Otepää has retained its charm—a picturesque landscape rich in history. Today, Otepää is renowned as the most famous winter sports center in the Baltic States, offering endless opportunities for recreation. Sporty Otepää buzzes with life all year round—during snowy winters, it earns the title of the Winter Capital, while in summer, its rolling forest trails and shimmering lakes attract anglers and beachgoers alike.

Ugandi Resto is part of Otepää’s story, offering warm hospitality and flavorful culinary experiences. In addition to the excellent sports opportunities provided by the local landscapes for decades, Otepää enchants visitors with its remarkable cultural heritage. Come to Otepää, where history, sports, and culture converge, and experience the beauty of the Winter Capital, a destination worth visiting all year round.