The daughter of a Mohawk chief in upstate New York and consort of a British dignitary, Molly Deganwadonti went on to become an influential Native American leader in her own right and a lifelong loyalist to the British crown before, during and after the American Revolution.

Born in 1736 at a time when the Mohawk, part of the larger Iroquois federation of tribes, were increasingly subject to European influence, Molly grew up in a Christianized family. In 1754, at the age of 18, she accompanied a delegation of Mohawk elders to Philadelphia to discuss fraudulent land transactions—a moment that is cited as her first political activity.

Molly met Sir William Johnson, a British officer during the French and Indian War who had been appointed superintendent for Indian affairs for the Northern colonies. After his wife died, she became his mistress. And although her race and class prevented them from being officially wed, they were common-law married and had nine children together. Johnson had acquired 600,000 acres of land in Mohawk Valley, and Molly, like other women of her time, came to manage a large and complex household, entertaining dignitaries both European and Indian. Their partnership proved politically fruitful, giving Johnson a familial connection to the powerful Iroquois tribes and earning Molly, who hailed from a matrilineal clan, increasing prestige as an influential voice for her people.

During the Revolutionary War, Molly and her family, like many Indians, sided with the British, who promised to protect their lands from colonists’ encroachment. Known as a persuasive speaker, she is credited with convincing Iroquois leadership to fall in with the British camp. Throughout the war, she acted as a spy, passing intelligence about the movement of colonial forces to British forces, while providing shelter, food and ammunition to loyalists. When they ended up on the losing side, Molly and her family fled for Canada, where she and other loyalists established the town of Kingston. After the war, the British paid her a pension for her services.

Anne Hennis Trotter Bailey, known as “Mad Anne,” worked as a frontier scout and messenger during the Revolutionary War. Originally from Liverpool, England, Anne sailed to America at the age of 19, after both her parents died. She eventually married a veteran frontiersman and soldier named Richard Trotter and settled in Staunton, Virginia.

Richard, who joined the Virginia militia as tensions between frontiersmen and Native Americans grew, was killed in the Battle of Point Pleasant, West Virginia in late 1774. After learning of her husband’s death, Mad Anne showed her mettle: She dressed in buckskin pants and a petticoat, left her son with neighbors—and sought revenge.

With rifle, hunting knife and tomahawk in hand, Anne became a scout and messenger recruiting volunteers to join the militia and sometimes delivering gunpowder to the soldiers. She couriered messages between Point Pleasant and Lewisburg, West Virginia—a 160-mile journey on horseback.

Her most famous ride took place in 1791. After soldiers at Fort Lee got word that the Native Americans were planning to attack, and discovered that their gunpowder supply was desperately low, Anne galloped to the rescue. She rode the 100 miles to Lewisburg, where she switched horses, loaded up with gunpowder and rode back to Fort Lee. Her journey was memorialized in an epic poem by militiaman Charles Robb, “Anne Bailey’s Ride.”

Anne remarried to John Bailey, a member of the Rangers, a legendary group of frontier scouts, in 1785. As the group worked to defend new settlements from Native American attacks, Mad Anne once again used her skills as a scout and courier. After her second husband’s death, she spent the rest of her days living a solitary life in the woods.

Rebecca Boone wasn’t the only formidable female in Daniel Boone’s family. His daughter Jemima earned her own spot in the history books on July 14, 1776. That’s when a Cherokee-Shawnee raiding group abducted Jemima, aged 14, along with two other girls while they floated in a canoe near their Kentucky settlement. Demonstrating their own knowledge of frontier ways, the quick-witted teens left trail markers as their captors took them away—bending branches, breaking off twigs and leaving behind leaves and berries.

Their rescue team, led by Daniel Boone himself, took just two days to follow the trail and retrieve the girls. The rescuers included Flanders Callaway, Samuel Henderson and Captain John Holder, each of whom later married one of the kidnapped girls. This event became such an integral part of frontier lore, author James Fenimore Cooper included it in his classic novel The Last of the Mohicans.

One of the best-known women of the American West, the native-born Sacagawea gained renown for her crucial role in helping the Lewis & Clark expedition successfully reach the Pacific coast.

Born in 1788 or 1789 in what is now Idaho, Sacagawea was a member of the Lemhi band of the Native American Shoshone tribe. At the age of 12, she was kidnapped by a war party of Hidasta Indians (enemies of the Shoshone) and taken to their home in Hidatsa-Mandan villages, near modern-day Bismarck, North Dakota. Around 1803, Sacagawea, along with other Shoshone women, was sold as a slave to the French-Canadian fur trader Toussaint Charbonneau. She soon became pregnant, giving birth to son Jean-Baptiste Charbonneau in February 1805.

Meanwhile, after the U.S. government had completed the Louisiana Purchase, which added 828,000 square miles of “unexplored” territory to America, President Thomas Jefferson dispatched Meriwether Lewis and William Clark to chart the new land and scout a Northwest Passage to the Pacific coast. After more than a year of planning and initial travel, the expedition reached the Hidatsa-Mandan settlement. Here they met Sacagawea and Charbonneau, whose combined language skills proved invaluable–especially Sacagawea’s ability to speak to the Shoshone.

Sacagawea, along with her newborn baby, was the only woman to accompany the 31 permanent members of the Lewis & Clark expedition to the Western edge of the nation and back.

Sacagawea proved invaluable to the explorers not just for her language skills, but also for her naturalist’s knowledge, calm nature and ability to think quickly under pressure. When a squall nearly capsized a vessel they were traveling in, Sacagawea was the one who saved crucial papers, books, navigational instruments, medicines and other provisions, while also managing to keep herself and her baby safe. In appreciation, Lewis and Clark named a branch of the Missouri River for Sacagawea.

Sacagawea died at the age of 25, not long after giving birth to a daughter. Clark became legal guardian to both her children.

While a woman named Susan Shelby Magoffin is often credited as the first white woman to travel the Santa Fe Trail, Mary Donoho made the trek 13 years prior. Leaving Independence, Missouri in 1833, Mary and her husband, William Donoho, headed to Santa Fe, bringing along their 9-month-old daughter.

Together, the Donohos created La Fonda, an inn for travelers at the end of the trail. It was here that Mary gave birth to two more of her five children—all of whom she eventually outlived.

Because married women of the time couldn’t legally own property without significant negotiation, it’s unlikely that Mary Donoho owned La Fonda. But with William gone on frequent trading trips, it’s believed that she operated the business largely on her own. In the west, women were gaining rights more quickly than back east, says Jane Simonsen, associate professor of history and women’s and gender studies at Augustana College. Despite the restrictive laws, “Women were still property owners—or sought to be—especially in the west. Later in the 19th century, with the allotment of land to Native Americans, women are given pieces of property that they owned in their own right.”

Believed to be one of the first two white women to cross the Rocky Mountains on foot, Narcissa Whitman left behind accounts of her life as a missionary in the Oregon territory with her prolific letters home to her family in New York State. She, her husband and others were killed by Indians in a savage attack on the mission.

Soon after marrying Marcus Whitman, a physician and fellow missionary in 1836, they left for Oregon Country and settled in what would later become Walla Walla, Washington. She wrote of the travails of rugged travel, such as fighting the current while fording strong rivers, and getting all of her belongings soaked each time. And she described learning of Indian ways: “There is a manner of crossing which Husband has tried, but I have not… Take an Elk Skin and streach (sic) it over you spreading yourself out as much as possible. Then let the Indian women carefully put you on the water, & with a cord in the mouth they will swim & drag you over.”

The Whitmans’ mission, officially begun in 1837, ministered to the Cayuse Indian tribe. Marcus held church services and practiced medicine while Narcissa taught school and managed their home. Already struggling with the unfamiliar customs of the Native Americans, she fell into a deep depression after her beloved toddler daughter drowned in the river behind her house. Her sorrow eased somewhat when she and her husband adopted a family of mixed-race children.

On November 29, 1847, tensions between the missionaries and the local Cayuse turned deadly. Accounts say that after Narcissa refused to share milk with some tribespeople—and shut the door in their face—they struck Marcus with a tomahawk in the back of his head, and shot and whipped Narcissa. In total, nine white people were killed and two more died days later. Scores were held hostage as the conflict, known as the “Whitman Massacre,” escalated into the Cayuse War.

In June 1846, after just eight months of marriage, 18-year-old Susan Shelby Magoffin and 45-year-old Irish immigrant Samuel Magoffin set off on a trading expedition along the Santa Fe Trail, a 19th-century transportation route connecting present-day Missouri to New Mexico. After Mary Donoho, Susan Magoffin was one of the first white women to travel that trail.

Susan, born into a wealthy Kentucky family (her grandfather was Kentucky’s first governor), kept a detailed travel diary that vividly chronicled the hazards of traveling the rugged byways of the American frontier. She detailed the plant life and terrain of her journey, as well as her personal challenges. On her 19th birthday, July 31, 1846, she lost a pregnancy, possibly due to a carriage accident. She wrote in her diary: “In a few short months I should have been a happy mother and made the heart of a father glad.”

Susan’s diary also discusses encounters with Native Americans and Mexicans who already occupied these lands. While initially disinclined toward the unfamiliar people she encountered, she writes about learning and adapting to their culture, including taking a “siesta” on a “buffalo skin with the carriage seats for pillows,” which she quite enjoyed.

Throughout Susan’s diary, she recounts the burdens of womanhood on the trails of the American West. She contracts yellow fever, loses another child, is responsible for setting up and maintaining homes, and finds herself repeatedly pregnant and uncomfortable. Susan writes, “I do think a woman emberaso [pregnant] has a hard time of it, some sickness all the time, heartburn, headache, cramps, etc, after all this thing of marrying is not what it is cracked up to be.”

By July 1847, 13 months after their journey began, Susan contracted yellow fever and gave birth to a son who died shortly thereafter. That September, Susan’s diary abruptly stopped. The Magoffins eventually abandoned their trading life and settled back in Kirkwood, Missouri. Susan Shelby Magoffin died in October 1855 at age 28.