The advent of the bicycle in the 1880’s stimulated great controversy about women’s proper role in society. Questions of "how they should ride", when they should ride, who they should ride with" were considered by commentators, and"wheeling’s" many critics were certain that bicycle riding threatened women’s health, morals, and reputation. Critics opposed wearing union suits (to absorb perspiration) or bloomers, and worried about the privacy and potential liberty bicycling granted to young men and women. Physicians Thomas Lothrop and William Poter posited that the bicycle inevitably promoted immodesty in women , and could potentially harm their reproductive systems. Other critics argued that women bicyclists favored shorter skirts, thus "inviting" insults and advances. Moreover, by tilting the bicycle seat, they could "beget of foster the habit of masturbation". For advocates like Maria E. Ward, however, "The bicycle (was) an educational factor . . . creating the desire for progress, the preference for what is better, the striving for the best, broadening the intelligence and intensifying love of home and country.

Before such noble attributes could be encouraged by "the wheel", change in dress or the design of bicycles was necessary. Skirts made riding the Ordinary (a bicycle with a large front wheel) virtually impossible. Tricycles, however, were designed to accommodate full skirts and allowed women to ride without adopting the bloomer outfit, which many women opposed for its politically radical associations. Like nearly every other aspect of life in the nineteenth century, tricycle riding had a specific set of rules and regulations. The rule against women riding alone in fact generated a new profession: the professional lady cyclist as chaperone. Tricycles were commonly used for touring, and the tandem tricycle was popular with couples.

The first bicycle was two equal-size wheels and a dropped frame with no crossbar was the Victor, first manufactured in 1887. With the addition of pneumatic tires (invented in 1889) and enclosed gear, women were able to ride comfortable without their skirts becoming entangled. The final dramatic improvement in bicycle technology was the coaster brake, invented in 1898. These features enabled women to bicycle safely without having to wear bloomers.

By 1900 bicycle manufacturers, sales agencies, and private individuals had opened women’s velocipede or riding schools in many northeastern cities. The Metropolitan Academy in New York City set aside a special area of its hall for women wishing to learn the mysteries of wheeling, and installed the first athletics-linked shower baths for women in America. The Michaux Club, a new York City organization founded in 1895, provided women with riding lessons in the morning, music to accompany indoor riding after lunch, and afternoon tea in the clubroom. The club also provided "ten pin rides" in which women demonstrated their skill by riding slalom-fashion through lines of bowling pins set on the floor. Indoor riding for women was more acceptable to critics than outdoor bicycling because it was controlled; there was neither the possibility of young couples riding off in private, nor any chance of immodest exposure of woman’s limbs. Men were excluded from the women’s bicycling sessions.

By the late 1880’2 two – or three-day tours under the aegis of regional or national cycling groups were common middle class activities. In both Europe and America these organizations charged small membership fees and issued road books which provided information about routes, road conditions, hotels, repair shops, and "consuls" – club members in towns and cities, appointed to answer the questions of touring cycles. Far fewer women than men belonged to these groups, but they evidently participated with equal enthusiasm. In 1888 the Philadelphia Tricyclists Club had 118 members, eighteen of whom were women. That year the club’s "Captain’s Cup", annually awarded to the member who covered the most miles during the year, was won by a woman "for her mileage record of 3,304 ¼ miles.