The Van Buren Sisters
In 1916, Augusta and Adeline Van Buren completed a 5,500 mile (8,851km) journey across the continental United States on separate motorcycles. They were also arrested multiple times for their villainous perfidy.
They had to contend with appalling roads, sometimes mountainous terrain, some remarkably unseasonal bad weather, and plenty of other issues... but they completed the trip, making them the second and third women respectively to cross the continental United States on motorcycles.
They were also the first women to reach 14,109-foot summit of Colorado's Pikes Peak by any motor vehicle.
SO, WHY WERE THEY CONSTANTLY BEING ARRESTED?
They were wearing trousers.
I don't mean that they should have been riding around with no pants on, as such... because that would have been chilly, and nobody wants flying bugs up their bits... but that even as late as 1916 there were expected dress codes, and women could be arrested for wearing men's clothes.
As the Van Buren sisters were wearing leather riding gear - including trousers and jackets - this was considered a ghastly breach of etiquette, not to mention the law, and couldn't be overlooked by... well, by the less-evolved members of society.
Technically, they should have been crossing the continental United States wearing dresses or skirts, and (probably) riding side-saddle... and according to media of the day, they were "using the national preparedness issue as an excellent excuse to escape their roles as housewives."
Ultimately the sister's petition to be allowed to be come dispatch riders was denied.
They each had successful later lives, however. Augusta went on to become a pilot, and Adeline became a lawyer.