To break up this sausage fest we’re throwing Bessie Stringfield into to the top 5, because she’s one of only a few women to ride a motorcycle so extensively in the 1930s, or in any decade for that matter. “The Motorcycle Queen of Miami,” as Springfield was known, is credited with being the first black woman to ride solo cross-country, completing eight solo trips in total, and serving as a U.S. Army motorcycle dispatch rider during WWII.