Highway44 begins in the Rural Municipality of Milton No. 292 at the junction with Highway7 on the north side of Alsask, just 1.2 kilometres (0.75mi) east of the Alberta border. It heads south as a paved, two-lane highway along the eastern side of town, passing by the former CFD Alsask and crossing a railway. Leaving Alsask, the highway continues south running parallel to the provincial border for a few kilometres before curving sharply to the east at the junction with Alberta Highway 570. Now crossing into the Rural Municipality of Chesterfield No. 261, where it traverses some slightly hilly terrain for a few kilometres, passing by the remains of Eyre before travelling through Mantario. Highway44 winds its southeast through a series of switchbacks through farmland to pass through Laporte, having an intersection with Highway635 before joining a concurrency (overlap) with northbound Highway21 to enter Eatonia. The pair pass by the Eatonia (Elvie Smith) Municipal Airport before crossing a railway line and making a sudden sharp right turn onto Railway Avenue and travelling through the southern side of town. Leaving Eatonia, the highway goes through another switchback to enter the Rural Municipality of Newcombe No. 260, having an intersection with Fairmount Road (Range Road 3245, provides access to the hamlet of Fairmount) before reaching the hamlet of Glidden, where Highway21 splits of and heads north at the intersection with Highway649. Highway44 winds its way southeast for a few kilometres to travel along the north side of Madison, paralleling a railway line as it crosses into the Rural Municipality of Snipe Lake No. 259.
Highway44 heads southeast through rural areas to pass through the hamlet of Snipe Lake, where it junctions with Highway658, before curving due east to enter the town of Eston, crossing yet another railway line as it traverses a business district on the north side of town along Railway Avenue. It has an intersection with Highway30 (2nd Street SE/NE) and makes two more railway crossings before leaving Eston, heading east through rural farmland for the next several kilometres, having intersections with Richlea Road (Range Road 3193, provides access to Richlea) and Isham Road (Range Road 3192, provides access to Isham) before travelling just to the south of Plato, where it has a junction with both Highway342 and Range Road 3183. Crossing into the Rural Municipality of Monet No. 257, the highway heads northeast to Greenan, where it makes another railway crossing, then eastward through Wartime to have a short concurrency with Highway4 on the north side of Elrose. Highway44 now heads northeast again through rural areas to pass through Hughton and Forgan before becoming concurrent with Highway664 and entering the Rural Municipality of Milden No. 286.
Highway 44 travelling over the Gardiner Dam
While travelling along the north side of Wiseton, Highway664 splits off and heads south while Highway44 heads northeast to have an intersection with Range Road 3123 (provides access to the town of Milden) on its way to Dinsmore, where it shares a concurrency with Highway42 as they travel along the town's south side and have a railway crossing. Splitting off and heading east, Highway44's pavement turns to gravel as it enters the Rural Municipality of Fertile Valley No. 285 and travels to the south of Anerley (access via Range Road 3102) before winding its way along the southern coastline of Stockwell Lake to the village of Macrorie, where it regains asphalt pavement and joins Highway45 southbound in a concurrency. With Highway45 splitting off just as the pair enter the northern fringes of the Rural Municipality of Coteau No. 255, Highway44 heads east past the Sandy Shores Resort to cross the South Saskatchewan River / Lake Diefenbaker via the Gardiner Dam to enter the Rural Municipality of Loreburn No. 254. Passing by Cutbank via a sharp right, the highway makes another sharp right at the intersection with Highway219 (Chief Whitecap Trail) and heads southeast along the shores of the lake to travel past Danielson Provincial Park before turning east through rural areas for several kilometres. It travels on the north side of the village of Loreburn, where it crosses a railway and has an intersection with Highway19, before crossing travelling through the very rural areas of the Rural Municipality of Willner No. 253, where it has an intersection with McWilldale Road (Range Road 3030, provides access to Kenaston) before entering the Rural Municipality of Arm River No. 252. The highway almost immediately curves northward and enters the town of Davidson, crossing a railway and joining Railway Street as a four-lane divided highway as it travels along the south side of downtown. Now making a sharp right onto Internal Road, Highway44 heads through neighbourhoods as a two-lane once again for a short distance before coming to an end at the junction between Highway11 (Louis Riel Trail) and Highway653.[3]
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