Veliky Ustyug and the west of the current territory of the Oblast, with Belozersk and Ustyuzhna, belonged to the Vladimir-Suzdal Principality and were constantly threatened by Novgorod.

In the 14th and the 15th centuries, the lands around Vologda became attractive for monks looking for desolate areas but still wishing to keep connections with the princes of Moscow.

The princes, in their turn, viewed the monasteries as means to keep the influence of the Grand Duchy of Moscow in its remote areas.

In the middle of the 15th century, the Vologda Lands were strongly involved with the Muscovite Civil War: Thus, Vasily the Blind was exiled to Vologda in 1446 and was released from his allegiance oath by the hegumen of the Kirillo-Belozersky Monastery, and by the late 1440s the Sukhona valley became the battlefield between the retreating army of Dmitry Shemyaka and the army of Vasily, chasing Shemyaka.

During the Time of Troubles, the area was ravaged by Polish troops, who at some point besieged Vologda but did not succeed in conquering the city.

In the 17th century, Vologda was a prosperous city located on the main trading route from Moscow to Western Europe.

During the reign of Tsar Peter the Great in the 18th century, Vologda became a shipbuilding center and played an important role in support of Russian military operations against Sweden.

On 4 July 1997, Vologda, alongside Bryansk, Chelyabinsk, Magadan, and Saratov signed a power-sharing agreement with the government of Russia, granting it autonomy.

Since 1991, CPSU lost all the power, and the head of the Oblast administration, and eventually the governor was appointed/elected alongside elected regional parliament.

As a subject of the Russian Federation, the Vologda Oblast has a certain constituent power, which consists of the right to adopt its charter, laws, and other regulatory legal acts.

In the period when they were the most important authority in the oblast (1937 to 1991), the following first secretaries were appointed[20] Since 1991, governors were sometimes appointed, and sometimes elected:[20] Legislative power is exercised by the Legislative Assembly of Vologda Oblast - a unicameral parliament of 34 deputies elected by a mixed electoral system (17 + 17) by the region's inhabitants for a five-year term.

Vologda Oblast is located on the East European Plain, and most of it represents forested hilly landscape.

Also, minor areas in the west of the oblast drain into the Oyat River which is a right tributary of the Svir and belongs to the basin of the Neva.

Lake Vozhe in the northwest of the Oblast, with its main tributary, the Vozhega, drains in the Onega River in the White Sea basin.

[28] 1.41 children per woman Total: 69.08 years (male: 63.85, female: 74.38) Babayevsky and Vytegorsky District in the northwest of the oblast belong to the areas traditionally populated by Vepsians.

[38] The biggest industrial enterprise of Vologda Oblast is the Severstal steel plant located in the city of Cherepovets.

Another traditional industries were salt production (around Totma) and glass making (in what is currently Chagodoshchensky District).

[39] In 1871, the Danish merchant Friedrich Buman opened a specialized butter factory in the manor of Fominskoye (13 km northwest of Vologda).

Other important paved roads include A114 highway, connecting Vologda to Cherepovets and Saint Petersburg, the roads connecting Vologda to Kirillov (the part which continues to Lipin Bor, Vytegra, and Pudozh, is partially paved), Vologda to Veliky Ustyug via Totma, Totma to Nikolsk via Imeni Babushkina, and Kotlas to Manturovo and eventually to Kostroma and Moscow via Veliky Ustyug and Nikolsk.

A branch from Konosha eastwards to Kotlas and further to Vorkuta, which crosses the north of the oblast, was constructed in the 1940s to facilitate the transport of coal from the Komi Republic.

Thus, Konstantin Batyushkov, a poet, was born and raised in his estate in Danilovskoye, but became a notable author after he moved to the state service to Saint Petersburg, and he only returned to Vologda (where he eventually died) after he developed a mental illness.

Igor Severyanin, a 20th-century poet, spent considerable periods of his life in the estate of his uncle, Vladimirovka, close to the city of Cherepovets.

In the 20th century, two of the authors of the Village prose movement in Soviet literature, which predominantly described rural life, were tightly connected with Vologda Region.

A poet Nikolay Rubtsov spent much of his life in Vologda Oblast before being killed in a domestic dispute in 1971.

Yury Koval, mainly known for his children's books, spent considerable periods of his life in Vologda Oblast.

Still, many buildings, including four classicist manors, survive, and make Vologda one of the biggest collection of wooden town houses of the 19th century in Russia.

Some of the best examples of rural wooden architecture are collected in open-air Ethnographic Museum in Semyonkovo, northwest of Vologda.

In contrast to many other Russian towns in the 1920s and 1930s, Veliky Ustyug was left intact and declared the national cultural heritage very early after 1917.

The relative desolation of Vologda lands attracted monks looking for solitude, resulting in numerous monasteries.

The Ferapontov Monastery, included into the World Heritage list, contains the only survived fully painted church in Russia with the frescoes of Dionisius.