The concept of a loess transportation surface portends that saltating sands deflate silt/dust and send them into suspension. This process continues until a topographic barrier stops the saltating sand, allowing loess deposits to accumulate downwind. This paper reports on loess transportation surfaces in west-central Wisconsin, USA. During the postglacial period, cold, dry conditions coincided with strong northwesterly winds to initiate widespread saltation of freely available sands, deflating any preexisting loess deposits. Large parts of the study area are transportation surfaces, and lack loess. Loess deposits were only able to accumulate at “protected” sites—downwind from (east of) topographic barriers, such as isolated bedrock uplands and the north-to-south flowing Black River. Loess in locations from these barriers is thicker (sometimes >5 m) than would be expected, and in places has even accumulated above preexisting loess deposits. For example, downwind (east) of the Black River, most of the low-relief landscape is covered with ≈40–70 cm of silty loess, even though it is many tens of kilometers from the initial loess source. Upwind of the river, on the transportation surface, the low-relief landscape is only intermittently mantled with thin, scattered deposits of silty-sandy eolian sediment, and generally lacks loess.