Osenewo is one of the oldest villages not only in the Gavrilov-Yam district but in the entire Yaroslavl region. The village is located on the banks of the Lachost River. The exact founding date of the village is unknown. Historians believe it was established during the Mongol-Tatar rule. One of the first documented mentions of the village dates back to the late 16th to early 17th century. In the 18th century, the settlement was granted village status, linked to the construction of the Church of the Mother of God of Kazan (1783), the largest and most majestic in the area. The temple, built on a high site, is visible from several kilometers away.

The village's heyday was in the second half of the 19th century until the early 20th century. Thanks to its advantageous location on the Suzdal tract, trade developed rapidly there. The village transformed into the second most important trading center in the region after Velikoselskoe. A few statistics: In the 1880s, there were 107 farms in Osenewo, and 405 people lived in the village; by 1914, the population had grown to 2,240.

There were 32 shops, an inn, tea houses, a guesthouse, and a post station. In the center of the village, near the church, there was a large marketplace. The largest and wealthiest markets took place twice a year during the Feast of the Mother of God of Kazan. Additionally, weekly fairs were held, known in the region as Sunday markets.