The Ride of Her Life: Maddening and Heartening in its Optimism

“I go forth as a tramp of fate among strangers.”

The Ride of Her Life is the true story of an elderly Maine farmer. Near to losing her family farm to taxes and upkeep, Annie Wilkins has recently recovered from pneumonia and been told she may have only a few years left to live. The town doctor has insisted she must “live restfully” and has found a spot for her in the county charity home.

A 2021 publication by author Elizabeth Letts, The Ride of Her Life begins as Annie sets out for California on a November day with a few saddle bags of canned goods, a few dollars, some camping gear, her dog, and a horse.

Oh, and she’s riding the horse.

It’s 1954, Eisenhower’s the President, television is new, and America is still covered with secondary roads. While some areas of the US continued to use horses for travel and corrals and stables were commonplace, many others were inaccessible on horseback. Heavy car and truck traffic were common. Not ideal for a senior citizen riding a skittish horse, but little about Annie Wilkin’s situation was ideal.

“You could think about everything Annie lacked: No parents, no children, not much health. No insurance, no bank account, no home. But she chose to focus on what she did have: Courage, loyalty, love in abundance.”

With unfailing optimism and the belief that people were basically good and would help a stranger, Annie Wilkins rode over 4,000 miles through snow, ice and across barren stretches of America. She was heroine to some, crazy to others but her journey made her fascinating to a 1950s populace obsessed with the pioneering spirit and weary of wars, cold or otherwise.

The Ride of Her Life is a story about one woman’s impossible journey. It’s also an ode to small-town America of the era when people would invite a stranger knocking at their door to share dinner and their roof. The town sheriff would put up a traveler at the jail for a night and provide breakfast. Towns rolled out the red carpet for Annie Wilkins. She spoke with schools, town councils and civic groups. She and her ever-loyal four-legged companions led parades and appeared on the Art Linkletter Show. She met and exchanged stories with Andrew Wyeth while he sketched her horse.

Annie’s character and her travels are extracted from diaries she kept during her journey and extensive correspondence she maintained with those she met along the way. Letts builds a narrative that is as compelling as any piece of fiction. More so, because this was an actual person who pursued an outlandish ambition against near insurmountable odds.

Lett’s rendering of Annie’s story makes for an upbeat, and mostly feel-good read, but I was conflicted by halfway in. Despite options for jobs and living situations extended to her, Annie always headed back for the road. SPOILER ALERT – She makes it to California, but eventually takes a bus back to Maine.

I appreciated Annie’s determination and the positivity that allowed her to keep going despite innumerable setbacks, but this wasn’t an entirely happy ending and there were casualties in her battle. It was a challenge for me to view empathetically such stubborn and often naive confidence. Like it or not, she endangered others, including her animals, with her mode of travel. Annie Wilkins is not a selfless character. She frequently disregards those more familiar with the geography and weather than her. I know I sound like a snob, and maybe worse, but this pushed buttons for me. I can’t decide if I was frustrated with Annie Wilkins or with my own experiences with similar levels of arrogance.

That said, independent and tough as I consider myself, faced with her choice, I might have taken the bed in the county home. I despise the cold and am shy of horses. The idea of setting out on such a journey is unimaginable to me. When I moved to New Mexico from New Hampshire, I had a warm vehicle around me, Nirvana on the radio and my trusty AAA maps.

Writers write for many reasons, but principally, to generate emotional response from the reader. Some novels stay with us not because we love the character’s story, we might, but more because they’ve made us analyze who we are. I’ve found myself saying, well, that <fill in blank for annoying task> might be rough, but at least I don’t have to cross the Rockies on horseback in a blizzard.

Annie Wilkins’ optimism, maddening and heartening, her story provides perspective for whatever challenges we might face.