325-Mile Henry Knox Trail Run from New York to Boston Rings in America250

Henry Knox led a 300-mile expedition during the winter of 1775, transporting 59 cannons from Fort Ticonderoga to Cambridge while crossing snow, frozen rivers and mountainous terrain. The successful delivery of that artillery helped force the British evacuation of Boston and marked the Continental Army’s first major victory, ultimately paving the way for freedom and the origins of a new nation.

Roughly 250 years later, eight runners from across the United States—including two current military service members (Marine Corps, Navy) and one veteran (Army)—are doing their best reenactment. In honor of the nation’s founding and to those who serve it today, the relay group hits the pavement on July 2 as part of a 325-mile ultra relay along the historic Henry Knox Trail—from Fort Ticonderoga, New York, to Harvard Square in Boston, Mass.

They will run day and night through historic small towns and the roads that helped shape the birth of the United States, concluding their endeavor Saturday, July 4, just in time to celebrate their achievements and the country’s anniversary.

“We have two active-duty military and one veteran,” James Doyle, one of the runners hailing from Chicago, told Military.com. “Although I didn’t serve, this event is still personal to me. My father, grandfather, great-grandfather, uncle and many other friends and family members have served our country, so supporting service members and veterans is something that means a lot to me.

“Even though I didn’t serve myself, this run is definitely a way that I can get back to our nation’s veterans and military families, and allows me to honor the generations of service members in my own family, while supporting those who sacrifice for all of us.”

Doyle explained that all runners are partaking under the Five to Nine brand, which celebrates ordinary people who commit time outside their regular 9-to-5 schedule to push their physical limits, show up for themselves, and support their communities. They host ultra relays across the country.

Their first race last year was a nonstop relay from Los Angeles to Las Vegas. This year’s race is even longer.

Running for a Good Cause

After the LA-to-Vegas experience, Doyle said they wanted to take on a new challenge that would test them physically and mentally but also carry a deeper purpose in running this historic route on our nation’s 250th birthday.

That includes raising money for service members, veterans, and military families through the Semper Fi and America’s Fund, of which Doyle has a family connection to the organization that provides lifetime support to wounded service members, veterans and their families.

“The fact that their support does not stop at one moment in time but continues throughout the veteran’s life really resonated with myself, my team, and [was] one of the many reasons why this partnership really is the perfect fit,” said Doyle, who ran the Chicago Marathon in 2025.

They’ve also secured a $1,000 corporate donation from the Capital District Physician Health Plan, which joined as a corporate sponsor to support the race local to the Albany area.

Running the Henry Knox Trail is a nod to history. Doyle said that he and his fellow runners are tracking trail markers across New England 250 years later as “a way to not only honor the people who helped establish our country’s independence, but the men and women who have served to protect that independence ever since.”

“Doing this on the Fourth of July makes the run especially meaningful,” he added. “It connects the history of our country’s founding.”

As of the afternoon of July 1, more than $4,000 had been raised through the Five to Nine website.

Getting the Logistics Right

While the run’s importance to the military community and to American history is obvious, the actual method of running from one state to another involved some planning.

Doyle admitted that logistically, it was “very difficult to plan” and took nearly a year to square all the details.

On Thursday morning, Doyle will fly in from Chicago and meet with others from Florida and the New England area at Fort Ticonderoga. The eight total runners will be split into two separate teams of four.

The relay itself is split into legs, with each leg amounting to roughly 40 miles.

“The first runner starts right at the first marker up in Fort Ticonderoga,” Doyle said. “They run a few miles, the van drives up with the other three runners. The runner runs their first few miles, then they tag in the next runner, and what we’ll be doing is we’ll be passing a baton—which is an American flag—as we go through our route towards Boston.”

‘Embracing the Suck’

Doyle was asked about how he and his fellow runners will be impacted by the national heat wave.

More than 175 million Americans, from the Midwest to the East, will be punched with high humidity and at risk of either “major” or “extreme” heat-related health issues, according to the National Weather Service.

While it’s not ideal, Doyle said physical sacrifice is part of the race’s goal.

“It’ll be tough, but we think that connects right back to our overall mission which is to be able to really push ourselves physically. … We’ll be staying hydrated—lots of fluids, lots of electrolytes, staying in the shade when possible,” he said.

“But at the end of the day, we’re ready to embrace the suck to make sure we get down to Boston in a timely manner to be able to celebrate.”