Saskatchewan has a transportation infrastructure system of roads, highways, freeways, airports, ferries, pipelines, trails, waterways, and railway systems serving a population of approximately 1,132,505 (according to 2021 census) inhabitants year-round.

It is funded primarily with local, rural municipality, and federal government funds.

80% of traffic is carried on our principal system of highways which is 5,031 km in length (20% of the total network).

— Saskatchewan Department of Highways and Transportation (See also Pareto principle.)

Early European settlers and explorers in Canada introduced the wheel to North America's Aboriginal peoples, who relied on canoes, york boat, bateaux, and kayaks, in addition to the snowshoe, toboggan, and sled in winter. Europeans adopted these technologies as Europeans pushed deeper into the continent's interior, and were thus able to travel via the waterways that fed from the St. Lawrence River Great Lakes route and Hudson Bay Churchill River route and then across land to Saskatchewan.

In the 19th century and early 20th century transportation relied on harnessing oxen to Red River carts or horse to wagon. Maritime transportation was via manual labour such as canoe or wind on sail and utilized the North Saskatchewan River or South Saskatchewan River routes mainly. Water or land travel speeds was approximately 8 to 15 kilometres per hour (5 to 9 miles per hour). Settlement was along river routes, and trade was locally concentrated initially on fur trading posts. Agricultural commodities were perishable, and trade centres were within 50 kilometres. Rural areas centred on villages, and they were approximately 10 kilometres (6.2 mi) apart. The advent of steam railways and steamships connected resources and markets of vast distances in the late 19th century.

Automobile and truck travel was employed in the early 20th century with highways and roads being under construction. The roadways ran parallel to the rail lines. The auto was abandoned in the depression years of the dirty thirties, and cars were towed by horse and became known as Bennett Buggies. The years following World War II showed much growth as the social economic lifestyle of Saskatchewan changed considerably. Gone were the farmers on each quarter section, and also leaving the prairie landscape were elevators. Grain storage elevators used to be required every 6 miles for loads by horse and cart. Combines introduced large scale farms, trucks introduced larger centres with a larger quantity of elevators. In the 1940s the branch rail lines were not economically feasible, were abandoned, and soon disappeared. As farms increased in size township roads and road allowances became part of the field.

Historically buffalo and Red River cart trails criss-crossed the prairies. Métis fur traders and brigades would follow these trails freighting supplies for the Hudson's Bay Company. Originally following trails created by bison, trails connected together trading posts, North-West Mounted Police forts and barracks. The Dominion government Boundary Commission Trail, the North-West Mounted Police Red Coat Trail, American–Canadian boundary trails, telegraph trail, railway trail, and rebellion trails were later trails. Due to the hard compaction of prairie sod, the remnants of this trail are still visible via satellite imaging to the trained historian eye.