maine farmer annie wilkins the ride of her life

Jackass Annie‚Äôs (Annie Wilkins) Remarkable Journey: A Tale of Courage and Survival‚ÄĚ

Maine Farmer Annie Wilkins

by Peter Barnes

This is the incredible and true story of a woman (Annie Wilkins A.K.A. Mesannie Wilkins), a horse, and a little doggie who embarked on a remarkable 7000-mile journey. They experienced a lifetime of adventures along the way and lived to share their extraordinary tale.


At the age of 63, Mesannie Wilkins, affectionately known as Annie, received devastating news from her doctor. Having recently overcome pneumonia, she was informed of a concerning spot on her lung. Uncertain whether it was cancer or tuberculosis, the doctor delivered a grim prognosis: she had only two years left to live if she chose to take it easy and follow a cautious path.

Aware of Annie’s dire financial situation, the compassionate doctor suggested the possibility of securing a place for her in a state-funded retirement home. Despite her reluctance to be impolite or unappreciative of the offer, Annie kindly informed the doctor that she would take some time to consider it.

Subsequently, Annie and the doctor embarked on a journey back to her modest farm in his grand and luxurious Packard. Throughout the drive, the doctor expressed his admiration for Annie’s tireless work and gently hinted that perhaps it was time for her to find some well-deserved rest.


It’s amazing how quickly everything can change, isn’t it?


annie wilkins Maine farmer amazing story

Life has a funny way of throwing unexpected surprises our way, reminding us to appreciate each moment and be ready for sudden shifts in our path.

As the doctor drove away, the boys from the nearby farm returned Annie‚Äôs little doggie to her. They had given him the playful nickname ‚ÄúDepeche Toi,‚ÄĚ which means ‚Äúhurry up‚ÄĚ in French, and the name stuck due to his lively nature. Annie tearfully kissed the little dog‚Äôs head, aware of the limited time they had together. With a mix of emotions, she opened the door to her house and stood there, taking a moment to survey her surroundings.

It wasn’t much of a house, more like a shack. The original farmhouse her grandfather had built had tragically burned down years ago. Annie’s current dwelling was an old outbuilding that was once used for storage in her grandfather’s time. With cracks letting the wind in and a small pot belly stove for warmth, she lived without electricity and relied on a well for water.

It’s remarkable how quickly everything can change. Just a few months ago, things were looking up for Annie. As winter approached, she was filled with anticipation for the upcoming spring. The year 1952 had been prosperous, with a bountiful harvest that allowed Annie and her Uncle Waldo to invest in some heifers, piglets, and a flock of hens.

Looking ahead to the upcoming spring and summer, Annie anticipated having cattle, pigs, and eggs to sell in addition to their grain. However, the primary challenge was surviving the harsh winter in Maine.

Unfortunately, Annie’s Uncle Waldo, at the age of 85, was unable to provide much assistance due to his advanced age and impaired vision. As a result, Annie took on the daunting tasks of breaking the ice, hauling the grain, and tending to the animals, working tirelessly from sunrise to sunset to ensure everyone was fed. Despite her determination, she couldn’t ignore the signs of her own deteriorating health.

Breathing became increasingly difficult, feeling like sharp ice shards with each inhalation. Walking became a struggle, often resulting in falls in the snow. However, despite the physical challenges, Annie mustered the strength to drag herself back to the house, refusing to give up.

In the aftermath of the blizzard, the boys from the neighboring farm rushed over on snowshoes to check on Annie and Waldo. One glance at Annie’s condition was enough for one of the brothers to immediately head towards the main road, a mile away, in search of an ambulance. Meanwhile, the other brother tended to the hungry animals that were patiently waiting. It was discovered that Annie had contracted pneumonia.

To cover the staggering costs of medical care, they had no choice but to sell off everything they owned‚ÄĒthe cattle, the pigs, and even the hens. If the situation wasn‚Äôt already devastating enough, Uncle Waldo tragically succumbed to his ailments, passing away quietly while Annie was battling pneumonia.

Now, Annie found herself completely alone in the world, facing the daunting reality of having just two years left to live.


Annie Wilkins had never been one to conform to conventional expectations


From a young age, she knew that working herself to exhaustion was not her desired path in life. Despite only attending school until the sixth grade, she had to leave education behind to assist her parents in running the small farm.

Day in and day out, she witnessed her family toil relentlessly from sunrise to sunset, striving to make ends meet from the meager resources the land provided.

The farm, tucked away in rural Maine, sat a mile away from the main road. It had been passed down from her grandfather to her parents, who dedicated their lives to its maintenance.

Witnessing the endless cycle of labor year after year, Annie yearned for something different. As soon as she was old enough, she seized the opportunity to escape the farm life, joining the circus as a bareback rider.

However, her plans took an unexpected turn when she received a letter informing her of her mother’s illness. Driven by familial duty, Annie made the decision to return home.

Uncle Waldo, despite not being a blood relative, had become an integral part of Annie’s life.

Originally hired as a farmhand to work alongside her father, he poured his hard work and dedication into maintaining the old farm. Following the passing of Annie’s father, a bond formed between Waldo and her mother, eventually blossoming into a romantic relationship.

During a difficult period, when the farm was struggling to sustain itself, both Annie and her mother took on jobs at a shoe factory to keep the farm afloat. Unfortunately, tragedy struck when her mother fell ill and passed away.

Left with only Uncle Waldo as her companion, Annie and he faced extreme poverty. In order to support the farm, Annie resorted to riding a mule to town, where she worked tirelessly to earn money.

It was during this time that the local community began labeling her ‚ÄúJackass Annie,‚ÄĚ likely due to her unconventional mode of transportation and her unwavering determination to support the farm against all odds.

Annie never adhered to society’s expectations of how women should behave. She refused to conform to traditional notions of femininity, disregarding conventional attire and displaying a bold and outspoken demeanor.

Her unconventional nature extended to her personal life as well, having gone through two divorces. In fact, she took a decisive stand when her last husband attempted to coerce her into signing over the farm. Firmly asserting her rights, Annie promptly kicked him out, making it clear that the farm was rightfully hers, bequeathed by her mother.

Annie‚Äôs independent spirit and refusal to conform to societal norms meant she was never fully accepted into ‚Äúpolite‚ÄĚ society. It was a reality she embraced, recognizing that people who were dirt poor like her rarely found a place within the confines of societal expectations.


Annie Wilkins, The Ride of her life


post cards of annie wilkins
Tramp of fate

As Annie stood in her small shack, her little doggie happily running around her, she couldn’t help but think about her hardworking mother.

Her mother had always talked about wanting to see the Pacific Ocean one day, but sadly, she never had the chance or the money. She worked tirelessly on the farm until she passed away and was laid to rest in the family cemetery.

Feeling a mix of frustration and determination, Annie made up her mind. She was going to fulfill her mother’s dream of seeing the Pacific Ocean, no matter what.

It was a way for Annie to pay tribute to her mother’s unfulfilled wishes and honor her memory, even if it meant that this would be her last adventure in life.

Annie took a big risk. She borrowed money by mortgaging her farm and used it to buy a retired racehorse named Tarzan. In November 1954, she dressed in men’s clothes, packed a small bag of clothes, and started her journey to California with Tarzan and her little doggie.

Annie didn’t have much with her, just a bedroll and some clothes. To make sure Tarzan had food along the way, she tied buckets of feed to him with string. She hoped that people all across America would be kind to her, an older woman traveling alone, as she set out to fulfill her late mother’s only wish.


Last of the Saddle Tramps


annie wilkins ride of her life journey
Minot Horsewoman nears halfway mark

Annie experienced incredible kindness from people she encountered on her journey. They offered her food and a place to stay. In small towns, she was allowed to sleep in the local jail, and hotels even provided her with a free room. Generous farm families opened their doors, providing her with food, shelter, and horse feed. Some people even gave her money, and a kind farmer even gave her an extra horse.

Day after day, Annie continued her ride, facing both good and bad weather. Sometimes her little doggie would ride on the horse with her, and other times he trotted beside her on a leash made from her clothesline. She traversed mountains and valleys, encountering various landscapes. Despite a man in Arkansas falling in love with her and proposing marriage, she remained committed to her journey, pushing forward.

Living on the farm, Annie had never experienced the hustle and bustle of big city streets filled with cars. The sight of all those vehicles scared her horse a lot. Along her journey, she caught the attention of journalists who were captivated by the story of a woman traveling thousands of miles on horseback.

It took Annie a whole year and 23 days to accomplish her mission. When she finally reached the magnificent Pacific Ocean, she stood there in complete amazement. Overwhelmed with emotion, she offered a heartfelt prayer for her beloved mama, grateful to have fulfilled her mother’s cherished wish.


Here’s the part that will touch your heart


When Annie began her journey, she saw herself as a woman with limited time left to live. She rode on her horse, feeling tired and weary, hoping that kind-hearted strangers would show compassion to a poor old woman without much money and not many years left to enjoy.

Annie would sometimes make fun of herself, comparing herself to an old frog sitting on a lily pad. She thought it was foolish to chase a dream and rely on the generosity of strangers she encountered.

However, as the miles passed by, Annie realized that it wasn’t just the farm she had left behind. There was something more meaningful and profound happening within her during this incredible adventure.

People gazed at her with sheer astonishment. They were filled with admiration for her incredible journey and labeled her an inspiration. She was not seen as just the old ‚ÄúJackass Annie‚ÄĚ disregarding the doctor‚Äôs advice.

With each passing mile, Annie’s posture in the saddle straightened. She no longer made fun of herself and began to feel a genuine sense of pride. She realized that she was truly accomplishing something extraordinary. The encouragement and cheers from people along the way uplifted her spirit. It was the adventure of a lifetime!

Journalists and reporters eagerly awaited her arrival in town, eager to hear her story. They offered to treat her to meals and wanted to document her experiences. To support her own journey, Annie started selling her own self-portraits and postcards, and to her delight, people eagerly purchased them and even asked for her autograph.

During an interview, Annie shared with the journalist that her second husband had left her because she refused to give him ownership of the farm. She mentioned that she should have handed it over to him and left a long time ago. In hindsight, it turned out to be the best decision she ever made.

In Missouri, a school invited her to speak to the students about her remarkable journey, and the newspapers were there to cover the event. To everyone’s surprise, she turned out to be an incredibly inspiring speaker. Yes, her!

As Annie stood before the vastness of the Pacific Ocean, tears of pride and joy streamed down her face. She was no longer the same woman who had left the farm more than a year ago.


The doctor’s prediction about Annie Wilkins was completely wrong!


Annie spent two years in California. During her time there, she had the opportunity to have dinner with Art Linkletter and became a small-scale celebrity. She became an inspiration to many and her story was featured in newspapers.

After two years, Annie returned to Maine, but not to her farm, as it had been taken by the government due to back taxes. Surprisingly, she didn‚Äôt mind. She made a stop in Minot, Maine, for a visit. People barely recognized her, as she was dressed up so nicely. Those who did recognize her still called out, ‚ÄúHey look, it‚Äôs Jackass Annie!‚ÄĚ But Annie just kept on going.

annie wilkins postcards
Annie Wilkins postcards from Minot Maine

Annie moved in with her good friend, Mina Titus Sawyer, in Whitefield, Maine. They had been friends for many years.

A decade later, Annie made the decision to turn her journal, photos, and postcards into a book. After all, why couldn’t she be an author? She had traveled 7000 miles on horseback all by herself. So she began writing.

Her book, titled “The Last of the Saddle Tramps“ was published in 1967. And there it was, her name right on the cover. She had become a published author!

Another book about her remarkable journey, titled ‚ÄúThe Ride of Her Life‚ÄĚ : The True Story of a Woman, Her Horse, and Their Last-Chance Journey Across America written by Elizabeth Letts, captured the incredible story of Annie‚Äôs adventure. You can buy if from Amazon >> The Ride of Her Life

It turned out that the doctor was wrong. Annie Wilkins lived for 24 years beyond the original prognosis he had given her. Instead of resigning herself to a state-run retirement home and waiting for her final days, she embarked on a journey of thousands of miles on horseback, witnessed the beauty of the Pacific Ocean, and even published a book.

annie wilkins postcards
Annie Wilkins postcards from Minot Maine

Annie Wilkins passed away in February 1980, just a few months short of her 89th birthday. She was laid to rest in her family plot at Maple Grove Cemetery in Minot, Maine.


Related: Annie Wilkins Amazing Story: The Ride of Her Life

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