Jeff Whittemore, Eric Strange and Tony Whittemore speak about making a documentary on the trip the brothers took at age 11 and 9, driving their pony car from their home in Massachusetts to the 1967 World’s Fair in Montreal.
Jeff Whittemore, Eric Strange and Tony Whittemore speak about making a documentary on the trip the brothers took at age 11 and 9, driving their pony car from their home in Massachusetts to the 1967 World’s Fair in Montreal. Credit: STAFF PHOTO BY ASHLEY SAARI—

When Tony Whittemore was 11, and his brother Jeff Whittemore was only 9, they hitched their Shetland pony, King, to the cart they used to deliver newspapers and set off for the 1967 Montreal World’s Fair – 350 miles away.

In a pony cart only going about 5 mph, it was a journey that took 27 days.

The Whittemores were guests of the Amos Fortune Forum on Friday, along with Eric Strange, a filmmaker who has made their story into a documentary.

In a deviation from the normal Amos Fortune Forum format, instead of a talk, the crowd was able to view Strange’s documentary, “Pony Boys,” a 24-minute film following the brothers on their journey across the Canadian border and the media sensation that followed them. Following the film, Strange conducted an interview with Tony and Jeff, followed by audience questions.

Tony said the idea came about when his elementary school principal informed his mother that he couldn’t read a map. Concurrently, he said he’d been begging his parents for a trip to Montreal to visit the World’s Fair, which sounded to a young boy something like Disney World. Tony said that his mother was “surprisingly upset” that his principal had implied he couldn’t do something, and when the two ideas collided and the prospect of Tony planning a route to Montreal to take the pony cart to the fair came up, he said his 11-year-old self wasn’t about to shoot down the opportunity.

“She had absolute faith that with proper preparation, we would get this done,” Tony said.

Their mother helped them learn to read the map, plot a route, and sent letters to every township on the route. The boys rode the cart in the annual Fourth of July parade, and the next day set out on their adventure. The trip included a stop in Jaffrey, where the Whittemores had a summer home. They were met in Jaffrey by Alfred Sawyer of Silver Ranch and his four-horse rig.

By the second day, they noticed a car following them. When Tony approached the car to find out what was going on, he found it was a reporter from the Boston Globe. It was the start of a media blitz. The boys were often met by crowds on their way into each town, and escorted by police to their bunk for the night at the end of the day. Sometimes, Tony said they didn’t make good-enough time to reach their intended destination, and would scout for a place – usually one with fences indicating a farm — and knock on the door, asking to be put up for the night with their pony. Tony said no one ever turned them down.

While the two said they received unprecedented generosity and welcome on their trip, their mother would sometimes receive letters or calls from disgruntled people who read about the journey and thought she was insane for allowing her two young children to undertake the trip alone. When they arrived in Montreal, the rest of the family received a sponsored trip to Canada to join their sons when exploring the fair. But while both remember some cool exhibits, they both agree the real adventure was getting there.

The next Amos Fortune Forum speakers are scheduled to be Littleton Alston and Ashley Olson. Alston is a professor of sculpture and Olson is the executive director of the National Willa Cather Center, and they will be speaking on  “Willa Cather as Creator: Breaking the Mold and  Carving a Place in History.” The talk will be Aug. 11 at 8 p.m. at the Jaffrey Meetinghouse.  There is no charge, but donations are accepted.

Ashley Saari can be reached at 603-924-7172, Ext. 244, or asaari@ledgertranscript.com. She’s on Twitter @AshleySaariMLT.