- 1 Moose Jaw — largest city in Southwestern Saskatchewan with 34,000 inhabitants; home of extensive underground tunnels and a mineral spa
- 2 Swift Current — regional city of 16,000; home to a Mennonite heritage village
- 3 Assiniboia — jumping off point to the Big Muddy Badlands
- 4 Chamberlain — small village at the intersection of Highways 11 and 2.
- 5 Maple Creek — the gateway to Cypress Hills Interprovincial Park
- 6 — small town known as the "Oasis of the Prairies"
- 7 Val Marie — the gateway to Grasslands National Park
- 8 Eastend – home to the world's largest known T-rex
- 1 Big Muddy Badlands — a dry prairie terrain with rocky outcroppings
- 2 Cypress Hills Interprovincial Park — a park straddling the Alberta-Saskatchewan border that has Canada's highest point between the Canadian Rockies and the Labrador peninsula
- 3 Grasslands National Park — protecting one of Canada's few remaining areas of undisturbed dry mixed-grass/shortgrass prairie grassland
- 4 Great Sandhills — a sparsely-populated rural region
- 5 Lake Diefenbaker and surrounding regions — 800 km of shoreline, three provincial parks and various regional parks for fishing, boating and camping
The southwest part of the region has some unique spots that are not typical of a prairie landscape. Straddling the border between Saskatchewan and Alberta, the Cypress Hills Inter-Provincial Park rises 600 m above the surrounding prairie and is home to a sub-alpine lodgepole pine forest. South of Leader, the Great Sand Hills Ecological Reserve is approximately 1,900 km² of ever-changing sand dunes. With 800 km of shoreline Lake Diefenbaker on the South Saskatchewan river is southern Saskatchewan's "Great Lake". The Big Muddy and Killdeer Badlands are very rugged hills and valleys carved by meltwater at the end of the last ice age.
Southwest Saskatchewan is the heart of Canada's own "Old Wild West".
The major industries are ranching and farming although the petroleum industry is growing in the western part of the region.
The Trans-Canada Highway (Highway 1) runs across the region from the west side at the Alberta border from Calgary, on-route to Regina and Winnipeg. There are several ports of entry from Montana, USA; however, none are open 24 hours.
As of February 2021, there is no passenger bus service in the region.
Despite the region's history being tied to Canada's first trans-continental railway, there is no passenger rail service in the region. The Empire Builder train runs about 100 km (60 mi) south of the US-Canada border.
The majority of trips through this region are by private automobile, and many places are only accessible by road.
Wood Mountain Post Provincial Historic Park, 8 km S of the village of Wood Mountain on Hwy 18 ☏ , tells the history of a North West Mounted Police (NWMP) post founded in 1874 to patrol the Canada/United States border and police whiskey traders, horse thieves and cattle rustlers. The post rose to prominence in 1876, when Chief Sitting Bull and 5,000 members of the Sioux (Lakota) First Nation took refuge in Canada after the Battle of Little Bighorn. Wood Mountain Post Provincial Park features two reconstructed buildings that tell the story of Major James Walsh of the NWMP and his negotiations with Chief Sitting Bull. Interpretive staff are on hand from June to September and school programming is available. There are picnic facilities on site and camping is available at nearby Wood Mountain Regional Park.
Prohibition Era rum-running in Moose Jaw's underground tunnels.
- Big Muddy Badlands, a series of badlands in southern Saskatchewan and northern Montana along Big Muddy Creek.
- Cypress Hills Interprovincial Park, an interprovincial park straddling the southern Alberta-Saskatchewan border; located southeast of Maple Creek, it is Canada's first and only interprovincial park.
- Fort Walsh, is part of the Cypress Hills Interprovincial Park. As a National Historic Site of Canada the area possesses National Historical Significance. It was established as a North-West Mounted Police (NWMP) fort after and at the location of the Cypress Hills massacre.
- Grasslands National Park, represents the Prairie Grasslands natural region, protecting one of the nation's few remaining areas of undisturbed dry mixed-grass/shortgrass prairie grassland.
- The Great Sandhills, a sand dune rising 50 ft (15 m) above the ground and covering 1,900 km2 (730 sq mi).
- T.rex Discovery Centre, natural history museum in Eastend which houses a number of fossils, including the remains of a Tyrannosaurus nicknamed "Scotty"
Explore the prairie and Badlands terrain in the region's national and provincial parks.
Fishing, boating and camping on Lake Diefenbaker.