Drive for travel within Russia and all over the world was in the nature of Vologda inhabitants since the first settlers were mentioned in the Russian north. The immigrants used rowing and sailing boats, coming mostly from the direction of Novgorod the Great. The way from Moscow to Arkhangelsk via Vologda very often required transporting boats by land, thus portages (carrying places between two navigable waters) developed. These portages became prototypes of modern highways.

The advantageous position of Vologda at the crossing of waterways helped numerous handicrafts and trade flourish. Progress continued despite ups and downs in activity. Restrictions on foreign trade through Arkhangelsk, authorized by Peter the Great, were completely revoked during the reign of Catherine II. By the end of the 18th century there were more than 70 factories in Vologda. The rope-yards alone numbered over 18. A special feature of Vologda industry was the production of tallow candles, delivered to Moscow and St.Petersburg by whole trains (strings of sledges). It would not be an exaggeration to say that no one in the Russian Empire managed without the brightly lit candle wicks from Vologda.

However the economic boom at the beginning of the 19th century was followed by a new recession in trade due to the appearance of new transportation routes. There is a commemorative slab kept in a museum of the town of Belozersk. It was taken from a monument erected in the first half of the last century, in honour of the end of Mariinsky by-pass canal construction. With the opening of this waterway Vologda was left out of the trade routes to St.Petersburg again. Its former importance returned only with the beginning of the era of railroads.

Laying of the first narrow-gauge line, connecting Vologda and Yaroslavl', attracted to the city a famous patron of art and businessman, Savva Morozov. The benefactor of Russian artists came to Vologda as a founder of the railway company. The railway began to work in 1872. Twenty six years later the road was extended up to Yaroslavl', and in 1906 the broad gauge railway traffic between St.Petersburg, Vologda and Vyatka started.

Today the Vologda railway junction is one of the biggest in the north-west of Russia. Trains going from Moscow to Arkhangelsk and Vorkuta, as well as from St.Petersburg to the Urals and further to the Central Asia, pass through Vologda. A direct route connects Vologda and Murmansk. In 1910 a famous Russian scientist and revolutionary, who spent many years in the cells of Schlisselburg fortress for participation in an attempt upon the tsar's life, Nickolai Morozov, flew to Vologda in a balloon and announced the beginning of the aeronautics era to Vologda citizens. Today planes of the Vologda state aviation company deliver people and cargoes not only within Russia but also abroad. The planes, AN-2 and AN-28, are used for tourist flights over the territory of Vologda, Veliky Ustyug and Kirilo-Belozersky architectural ensemble.

Several highways of federal importance run through the region from Moscow to Archangelsk and from Vologda to New Ladoga, comprising 11,000 km of surfaced roads. It is difficult to imagine the Russian transport network without the gas main "Northern Lights", also running through the Vologda region.

The Volga-Baltic Waterway going through the Oblast enables businessmen to ship goods to ports of the Baltic, White, Caspian, Black and Mediterranean seas.

The Vologda Oblast transportation network paves the way for business to reach vital markets and suppliers and provides employees with a variety of efficient commuting and freightage options.

The road system's share of passenger transportation is 96,9 % of the total portion of passenger traffic. Railroads are the dominant mode of freight transportation.

The transport system of the Vologda Oblast includes a network of bus routes accounting for 25,600 km; 8 routes of intercity electric transport totaling 74,600 km; railway net of common use making up over 769 km; inland waterways extending 1577 km and airlines accounting for 9,500 km.