Harley-Davidson's intention in introducing a new middleweight model was to increase the size of the motorcycle market by appealing to new riders with an entry-level product.

[5] The design imitated the British Douglas motorcycle flat-twin with cylinders in line with the frame,[1][3][5] and offered several features that were meant to bring new motorcyclists into the market, including a smoother running engine than a typical Harley-Davidson V-twin, a lower center of gravity for easier handling, and a design that kept the rider and the motorcycle cleaner from oil and the dirt that oil attracted.

[2][5][6] A contractor rode a Model W 1,200 miles through Death Valley surveying sites for hotels and rail lines, without problems with the motorcycle.

[6] Hap Scherer, a publicity manager for Harley-Davidson,[6] set record times on endurance runs from British Columbia to Tijuana and from New York to Chicago.

[2] The Model W never sold well in the United States,[2][3][6] and the expected crowd of new riders taking up motorcycling on Sport Twins did not appear.

[5] In 1920, a year after the introduction of the Model W, Indian began offering their Scout, which was similar in size, faster, and much more popular.