When a teacher tells a mom her 9-year-old son can’t read a map, her fix is as audacious as it is inspiring.
She sends him and his 11-year-old brother on a 317-mile journey to the World’s Fair in Canada—armed with nothing but a Shetland pony, a cart, and each other.
No cash. No adults.
It’s like “Huckleberry Finn” meets “Free Solo”!
Thanks to Jason Kottke for the tip.
Trailer for “Pony Boys”
Watch “Pony Boys”
You can watch “Pony Boys” on Facebook (click the video embed link above) or directly on the New York Times site (with ads) at https://www.nytimes.com/video/opinion/100000008461716/pony-boys.html
It looks like it’s also on OVID (with a subscription)
You can find the latest streaming options at https://www.justwatch.com/us/movie/pony-boys (though I find that they don’t include Facebok or many YouTube videos) .
Ratings:
- My Rating: 90/100
- IMDB Rating: 8.7/10
- Rotten Tomatoes Ratings: na
Release Date: 2022
My Review of “Pony Boys”
In 1967, a Massachusetts mom named Wendy Whittemore was hit with surprising news: her 9-year-old son, Jeff, couldn’t read a map.
It wasn’t something she discovered herself; it was his teacher who pointed it out, casually suggesting that Jeff might need more practice. But Wendy wasn’t one for passive parenting. Instead, she came up with a bold plan.
Wendy encouraged Jeff and his older brother, 11-year-old Tony, to take a trip—on their own—by pony cart from suburban Boston all the way to Montreal’s World Fair.
Armed with a tent, a Shetland pony named King, and Wendy’s unwavering confidence, the two boys set off on an adventure unlike any other.
You can’t make this sh*t up: A mom heard her son couldn’t read a map, so she sent him on a 317-mile road trip to fix it.
The journey unfolded in ways nobody could have imagined. Although the boys were traveling solo, the kindness of strangers transformed the experience. As they passed through towns, people were drawn to the two young adventurers in their pony cart.
Locals offered food, beds, and encouragement, ensuring the boys never even had to pitch the tent they’d brought along.
Their adventure, however, wasn’t without its critics. Wendy received calls and letters from people accusing her of endangering her sons. Yet she stayed firm, believing her sons were learning lessons no classroom could offer.
Eric Stange, the director (knugh archival photos, news clippings, and present-day interviews with Tony and Jeff, who are now adultsown for “The War That Made America”, Unnatural Causes”, and “James Baker: The Man Who Made Washington Work”) brings this wild parenting gamble to life thro.
Stange doesn’t treat the story as mere nostalgia; he’s interested in Wendy’s vision as a parent who saw value in trusting her kids with freedom and responsibility. It’s clear her gamble paid off.
Border Drama and VIP Treatment
Not every part of the trip was easygoing.
When they reached the Canadian border, customs officers didn’t know what to make of two kids traveling alone with a pony.
They asked where the boys planned to stay that night—a question that stumped Tony and Jeff. Not surprisingly, they had no fixed plans, just a map and a destination.
The border agents refused them entry until Wendy stepped in and convinced officials to let her sons and King pass through.
Arriving at the World Faire
Once they arrived in Montreal, things took a surreal turn. The boys were met by the press, who were fascinated by their story, and received special “VIP” treatment at the World’s Fair, though they had to ask their mom what “VIP” even meant.
They were shown exhibits that included a futuristic car that could unfold and reassemble itself automatically.
Even King was captivated, trotting up to a towering Mountie horse in awe at his new, massive friend.
A Mom’s Faith in Adventure’
Reflecting on the trip, Jeff says: “The real adventure was the trip up there.”
Tony, looking back, he believes his mother’s influence shaped who they became, saying:
“The person who had the most effect on who we ended up being was my mother. She taught us if you’re willing to work hard and use common sense, you’ll always be able to get the job done. And dang, if that isn’t true!”
Tony Whittemore
Wendy’s faith in her sons’ resilience is the backbone of “Pony Boys.” In a time when kids had more freedom, she trusted her boys to navigate the journey, even as people around her voiced doubts.
Stange’s film captures this blend of bravery and parental faith in a way that feels both nostalgic and refreshing.
Wendy’s decision wasn’t about abandoning her kids to fate; she believed they were capable and wanted to show them what they could achieve.
Watching “Pony Boys” in today’s world, where kids are rarely given such freedom, you’re forced to wonder if we’ve gone too far in the other direction. Would I send my own kids on a trip like this? Likely not.
But seeing how the Whittemore brothers thrived on their journey makes you question if we’re missing something essential by being so protective.
Tony and Jeff didn’t just reach the World’s Fair—they proved their strength, resourcefulness, and independence, qualities that no amount of supervised playtime could instill.
Wrap Up
In “Pony Boys,” Eric Stange crafts a story that’s as heartwarming as it is thought-provoking.
It’s a tribute to Wendy Whittemore’s boldness as a mother, trusting her sons with an adventure that would change their lives.
For Tony and Jeff, the journey was the true reward—a test of their independence and resilience that they would remember forever.
By the time they reached Montreal, their understanding of themselves and the world had deepened in ways that went far beyond geography.
It’s a story that feels almost impossible today, but Stange’s film reminds us that sometimes, the best life lessons come from taking risks and going the extra mile.
If you want to learn more about the Pony Boys, check out PonyBoys.net
Thanks for reading!
Rob Kelly, Chief Maniac, Daily Doc