In the summer of 1916, the United States was poised to enter the First World War. Two New York sisters, Augusta Van Buren, 24, and Adeline Van Buren, 22, were eager members of the Preparedness Movement, a campaign dedicated to strengthening American military readiness at home in anticipation of joining the conflict in Europe. Gussie and Addie were born into privilege and a life of high society but nevertheless had a pronounced adventurous streak. They learned to fly airplanes, could handle themselves in a boxing ring, raced horses, and rode motorcycles. The sisters decided that though the military wouldn’t allow women weren’t near combat lines, they would make excellent dispatch riders—motorcycle couriers, basically—racing between intelligence outposts and the front lines to deliver necessary communications. Gussie and Addie figured this would be a way into serving the military during wartime, as they’d free up men for combat duty.

These were dangerous positions, as they’d be valuable targets, riding in dismal conditions, but the Van Burens were confident their motorcycle skills and toughness gave them all the experience they’d need. First, however, they’d have to convince the military that women could serve that role successfully.

So they hatched a plan.

They’d be on their own, left to figure out how to navigate, resupply, source petrol, and defend themselves. Bandits still held up stagecoaches in the more desolate parts of the highway.

The sisters decided to ride coast to coast, from New York City to San Francisco, as a demonstration that women could serve as dispatch riders as well as any man. This at a time when female motorcyclists weren’t exactly unheard of but were still rare enough that only a decade before, the magazine Motorcycle Illustrated ran a headline that read, simply: “Detroit Has a Female Motorcyclist.” As in one. In all of Detroit.

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This was also long before paved highways and the infrastructure to support motorized travel existed across much of the United States, especially in the West. There were few places to get fuel, water, or food. The sisters decided to follow the newly christened “Lincoln Highway” stretching from Manhattan to the southern shores of the Golden Gate in San Francisco, but “highway” today denotes perhaps a grander road than actually existed then. Much of it was simply rough dirt tracks. They’d be on their own, left to figure out how to navigate, resupply, source petrol, and defend themselves. Bandits still held up stagecoaches in the more desolate parts of the highway.

To prepare, Gussie and Addie went on long-distance rides in New York, growing accustomed to long days in the saddle and exposure to elements, testing their gear and clothing, gradually increasing the distance they rode until finally they were ready.

On July 4, 1916, the sisters climbed aboard their top-of-the-line bikes, courtesy of Indian Motorcycles. They each rode the Powerplus model (which sold for $275), a 1,000cc machine with a top speed of 65 mph, a webbed frame that allowed for a bit more suspension travel, and gas headlights (likely acetylene), which meant they’d be able to charge ahead through pitch black nights in the still almost completely rural West. These were simple but rugged motorcycles capable of mixed terrain travel. They wore only leather caps, sturdy goggles, leather jackets and britches, and calf-high boots. From Brooklyn’s Sheepshead Bay racetrack, they set off, bound for San Francisco, some 3,800 miles of hard riding away. Just three days earlier, in France, the horrific fighting at the Battle of the Somme began.

“There were no road maps west of the Mississippi,” their great-nephew Robert Van Buren once said of his aunts’ trip. “The roads were just cow passes, dirt trails, wagon trails, things like that.”

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After an uneventful beginning of their journey, things took a turn for the absurd and difficult once they reached the Midwest.

At the time, in many towns, especially in rural America, women wearing pants was a serious violation of the social order. Gussie and Addie were just out of Chicago, barreling west through the ring of small townships that radiated from the city through central Illinois, when they were pulled over by police for their scandalous dress and cited for wearing men’s clothing. This pattern was repeated several times as the sisters roared into towns unaccustomed to women on motorcycles, especially women unaccompanied by men, and definitely not accustomed to women on motorcycles, without men, wearing pants. Still, they persisted.

Though they’d hoped to reach San Francisco by August, the sisters, delayed by weather and repeated run-ins with the law, arrived in the Rocky Mountains in August, a month after they’d set out. Gussie and Addie, in a “to hell with it” moment, decided to take a detour and ride to the summit of Pikes Peak, at 14,109 feet, not an easy ride with the motorized vehicles of their day. In doing so, they became the first women to reach the Pikes summit by any kind of motorized transport. From there, they beelined as west as they could over the Rockies, trudging up isolated trails softened and slickened with mud during torrential afternoon rains. Eventually, their motorcycles stuck fast in sticky mud and the sisters were forced to abandon their bikes and walk on foot to Gilman, a mining town filled with men shocked to see two young women emerge from the hills, freezing and wearing mud-splattered leathers.

The miners helped the Van Burens free their motorcycles, which they proceeded to dump repeatedly in the impossibly wet trails, as they headed further west. The arid high desert near Salt Lake City nearly proved to be the end of them after they lost their trail in a dust storm and became disoriented, stalling their progress. A passing prospector, his horse-drawn cart loaded with water and food, quenched their thirst and pointed them in the direction of safety.

Finally, on September 2, the pair rolled into San Francisco. They’d covered 5,500 miles and taken twice as long as they’d hoped to arrive, but braving horrendous conditions and the consternation of befuddled policeman along the way, the Van Buren sisters had become only the second and third women to complete a coast-to-coast motorcycle adventure. Still, with a bit of gas in their tanks, they decided to extend the trip even further, motoring south along the coast, clear to Tijuana, Mexico.

The media cheered the Van Buren sisters upon completing their journey, but a great deal of attention was paid to the motorcycles, not the riders. Some newspapers accused them of playacting, galavanting around in tight khaki trousers and boots to “display their feminine counters in nifty khaki and leather uniforms.”

Worse yet, for the Van Buren sisters, the military rejected their application for duty as dispatch riders. Three years before women won the right to vote, many sectors of society still weren’t ready to accept women in unfamiliar roles.

Unfazed, they went on to fulfilling lives. Gussie served as a pilot and a member of Amelia Earhart’s Ninety-Nines, a group dedicated to burgeoning the ranks of women pilots. Addie earned a law degree and became an attorney at a time few women went to college, let alone practiced law.

Still, they left their mark on motorcycling and adventuring. In 2002, the sisters were elected to the AMA Motorcycle Hall of Fame. Today, women and men go on memorial cross-country rides in honor of them.  And a line Gussie once told a reporter about their trip, is oft-printed on t-shirts and bumper stickers: “Woman can, if she will.”