“Mark me,” the tale I am about to tell is indeed one of epic proportions. A tale of a man defeated, but who escapes death with the help of a certain female heroine. A tale of truth. We explore how the Bonnie Prince Charlie inspired a nation, a movement, a young woman, and the song of a lad that is gone.
This post may contain outdated language to cultural and disability descriptions that are used in the show. We use these terms to remain consistent with the verbiage used in the show and books.
But first, a little history lesson.
See that guy on the left? Well, actually the guy on the right…


…that’s Charles Edward Stuart. AKA, Bonnie Prince Charlie. He is known for leading the Jacobite rising of 1745.
You see, his grandfather was King James II of England and VII of Scotland, until he was exiled from the throne in 1688. A Bill of Rights passed in 1689 and an Act of Settlement passed in 1701 prevented any Catholic from sitting on the British thrones.
After James II died, Charles’ father, James Francis Edward Stuart, claimed the English, Scottish, and Irish crowns. He was known as James III in England and Ireland, and James VIII in Scotland. He obtained the titles with the support of Jacobite followers, and his cousin, King Louis XIV of France. But during the Jacobite rising of 1715, he failed to claim the British and Irish thrones.
Phew! There’s more Roman numerals in there than an ambitious 10th grader outlining their latest English assignment, but what can I say? The aristocracy weren’t exactly known for creativity in naming their kids.
Enter the Fresh Bonnie Prince
Following his failure, James named Charles Prince Regent in 1743, giving him permission to act in his name. He spent some time traveling through Rome and Paris, gathering support for a Stuart restoration. He set sail then, to Scotland, where many Highland clans, both Catholic and Protestant, still supported the Jacobite cause.
With enough support for a serious rebellion, Charles, and his army, won the Battle of Prestonpans on September 21, 1745. The battle, which lasted less than 30 minutes, established a revolt against the British government. It was the first significant battle in the Jacobite rising of 1745.

The Battle of Culloden
Following their significant win at Prestonpans, and another victory at the Battle of Falkirk Muir, Charles Stuart and his army of 5,000 men were not prepared for what lay ahead on Culloden Moor.
A British army of 9,000 men, led by the Duke of Cumberland, were ready to take on the Highland charge, armed with bayonets, a cannon, and six mortars.
Ignoring advice from general Lord George Murray, Charles chose to stay and fight on the exposed, marshy ground. As a result, 1,000 – 1,500 of his men were killed in battle on April 16, 1746. Many more were wounded. In comparison, Cumberland’s army only lost 50 men.
The Highland way of life was forever changed. A consequence of a failed rebellion against the crown, The Dress Act of 1746 banned the wearing of tartan and kilts in Scotland. This time in history became known as the Proscription Period.

Escape of the Bonnie Prince
Realizing his impending defeat, Charles Stuart abandoned the Jacobite cause amidst the battle, and hid in the moors of Scotland, just barely a step ahead of government forces. A £30,000 reward was issued for his capture, but the Highlanders did not betray him. Instead, they aided him in his escape.
After two months on the run, Charles arrived in Benbecula where he met 24-year-old Flora MacDonald. She was well aware of the Bonnie Prince’s whereabouts from her benefactor, Lady Clanranald, a Jacobite sympathizer. After some initial hesitation, she agreed to help.

Disguising the Bonnie Prince as her Irish spinning maid, Betty Burke, she obtained permission from the English to sail to the Isle of Skye with a small crew.


Over the Sea to Skye
After a successful voyage, they hid overnight in a cottage before making their way to Portree, where the Bonnie Prince boarded a ship to France. He spent the rest of his life traveling around Europe, trying to revive his cause. Unable to reclaim the English throne, he finally settled in Italy, where he died of a stoke in January of 1788. Legend says the Bonnie Prince presented Flora with a locket containing his portrait as a token of gratitude.
After learning of the escape, the English arrested Flora for helping the Bonnie Prince. She spent a year imprisoned in the Tower of London before receiving a general pardon from the British government.
The “Skye Boat Song” is a commemoration and account of the Bonnie Prince’s daring escape in a small boat, dressed as a woman, with the help of Flora MacDonald. The song’s popularity contributed to the romanticization of the Bonnie Prince as a Scottish hero.
As famous as Charlie’s bonneted escape was, memorialized in song, could this have been the inspiration for Rochester’s donning a dress to fool his house party guests in Charlotte Bronte’s Jane Eyre? It’s fun to pretend it was.
The original chorus lyrics were:
“Speed, bonnie boat, like a bird on the wing,
Onward! the sailors cry;
Carry the lad that’s born to be king,
Over the sea to Skye.“
Flora’s Adventures Continue
After her release, Flora returned to Scotland where she married her fiancée, Allan MacDonald. In 1774, they travelled to the New World and settled in North Carolina. Wilmington gave a ball in her honor that was a smashing success. Eventually, Allan bought land in Anson County where he and Flora built a home and named it Killiegray.
Ironically, a supporter of the British during the Revolutionary War, she spent her time rallying the Scots living in North Carolina to support British officer, Donald MacDonald. Allan fought under MacDonald during the war, but enemy forces captured him at the Battle of Moore’s Creek Bridge on February 27, 1776. He was imprisoned at Halifax for a short time before being transferred to Pennsylvania.

Forced into hiding, Flora lost everything as American rebels burned down the family home. She sold a silver tea service and other gifts she’d received while imprisoned, to secure passage on a British man-of-war headed back to Scotland.
During the voyage, French privateers attacked the ship. Flora sustained an arm injury after refusing to go below deck during the fight.
Once back in Scotland, she lived at Dunvegan Castle on the Isle of Skye. Allan joined her there after his release in 1783.
Flora died on March 5, 1790. Her body was wrapped in a sheet the Bonnie Prince once slept in, and she was laid to rest at Kilmuir on Skye.
What are some fun “mark me” moments in your life? Before Outlander, did you know about Bonnie Prince Charlie’s daring escape?
Meet the Writer

Tori Carpenter, 24, is an upcoming graduate of Kent State University. She has a passion for creativity and a love for all things Outlander. She discovered the STARZ hit series in March of 2020 and, subsequently, the book series. It offered an escape at a time when the whole world felt isolated. She currently resides in Northeast Ohio in her family home where she grew up with an appreciation for history. She is a nanny for four-year-old twins and a photographer in her free time. You can always find her at the gym or snuggled up with her beloved dog, Harrison, a three-year-old Goldendoodle who shares her birthday. Follow her on Instagram and Twitter (@victoria_jane13) and on Facebook and LinkedIn (Victoria Carpenter).
Sources
https://www.nam.ac.uk/explore/battle-culloden
https://www.historic-uk.com/HistoryUK/HistoryofScotland/The-Battle-of-Prestonpans/
https://www.britannica.com/biography/James-Edward-the-Old-Pretender
https://www.historic-uk.com/HistoryUK/HistoryofScotland/The-Two-Pretenders/
https://www.historic-uk.com/HistoryUK/HistoryofScotland/Flora-Macdonald/
https://www.britannica.com/biography/Flora-Macdonald
https://www.ncpedia.org/biography/macdonald-flora-0
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