The first performance of the automobile in Ann Arbor was hardly indicative of its ultimate impact. Hoping to obtain a franchise, Staebler and Son, well established bicycle dealers, received a demonstrator Trimoto on October 9, 1900. It had three wheels, a gasoline engine, and weighed about 500 pounds. It carried two people and reached a top speed of twelve miles per hour. On December 20 Edward Staebler wrote despondently to the manufacturers: "I cannot use the Trimoto to go between my residence and the store for there is a hill to climb which the machine has climbed but twice out of many trials and we do not care to try any more because of the jeers from the onlookers."

In 1901 the Staeblers traded the Trimoto for a Toledo Steam Carriage. The Steamer was more successful at climbing Ann Arbor's hills but broke down nearly as often as the Trimoto. At the end of 1901, the Staeblers were still the only automobile dealers in town and had only the Toledo Steamer to demonstrate. Three other cars appeared in 1901. One, a steam car, was built by Ann Arbor resident Howard Coffin, a student in the Engineering College. Coffin's steamer, which participated in the Labor Day parade of 1901, was assembled in the Staebler bicycle shop.

Automobiles were slow to catch local fancy. Edward Staebler noted in 1906 that, "This is a peculiar town. Our population is 18,000 and we have not over a dozen machines here. Half of those are used but very little." Eventually, however, the flexibility and mobility of the automobile won converts. In 1908 there were forty cars in Ann Arbor and in 1910, Mayor William Walz issued the first rules for driving and parking. Service industries related to the automobile grew as older trades declined. In 1901 the city boasted nine blacksmiths, nine bicycle shops, and nine liveries. By 1919 there were four blacksmiths, one bicycle shop and no liveries. In 1912 Walker's Livery was the city's largest livery with more than thirty horses. The livery was famous for two teams of pure white Arabians which were rented for funeral processions. The horses and equipment were auctioned off in 1914 and the livery became the Ann Arbor Taxicab and Transfer Company. In 1919 fifteen establishments called themselves automobile garages, nine firms advertised automobile repairs, and four advertised automobiles for hire.