Starting at Interstate 41/US Highway 41 (I-41/US 41) at a diamond interchange, WIS 144 proceeds to travel northward.

Also, the Kettle Moraine Scenic Drive runs concurrently with part of the highway.

It travels adjacent to Big Cedar Lake.

In West Bend, WIS 33/WIS 144 then meets US 45 at a diamond interchange.

Then, in downtown West Bend, WIS 144 branches off northward along the riverfront of Milwaukee River.