[11] The seat in Odoyev, as the successor of Novosil, was considered the senior of the Upper Oka principalities.

Odoyev's history was closely associated with its geopolitical location between the Grand Duchy of Lithuania, Moscow and the Golden Horde.

[13] The Duchy of Odoyev had trade relations with the Horde, selling beaver and marten fur and honey and importing pottery, coins and iron caldrons.

The treaty implied that Vytautas would not attack the lands of the Princes of Novosil and Odoyev, while the latter would be his vassals and serve to him, assisting in his foreign policy.

[17] The Princes of Novosil and Odoyev had the right to break the treaty in case of no desire to prolong it or violation of its conditions, upon the death of one of the parties.

[17] The Princes of Odoyev were given large lands in the Grand Duchy of Lithuania under the condition to pay yearly tribute from them.

Prince Fyodor Lvovich was marked by anti-Moscow policy and even planned a plot against Vasily II.

[19] Since the end of the Lithuanian-Moscow war of 1433 — 1453, the situation had changed for the Upper Oka principalities.

[22] But as early as in 1645, Odoyev was neglected, the towers of the fortress lost their roofs, the bridge had decayed, while the water well was empty.

[15] By the early 1800s, the population of Odoyev was two thousand; the town had seven churches, seven taverns, and six plants, while in 1838 the first girls' boarding school in Tula Governorate was opened here.

[22] Odoyev was famed for its gardens; almost every resident of the town owned one and it was covered in vegetation.

The legend has it that the pastila from Antonovka apples from Odoyev was served at the dinner of Ivan the Terrible.

[22] In the early 16th century Princes of Vorotynsk built the Monastery of the Nativity of the Holy Mother, closed down in the 1700s and ruined in the Soviet times.