Cinch I.T. and Why Me and Sherry’s House’s 100 Mile Ruck March Honors Milestone with Upcoming Documentary
Featured in: Chamber Exchange – The Newspaper – November 2025 Edition – Worcester’s Chamber of Commerce Quarterly Publication
What started as a creative solution during the height of the pandemic has grown into one of Central Massachusetts’ most inspiring annual traditions. This past July, Cinch I.T. with Why me and Sherry’s house, hosted the fifth annual 100 Mile Ruck March Charity Challenge, a four-day endurance trek that unites athletes, veterans, and community members in one powerful mission: to raise money and awareness for Why Me & Sherry’s House, a local nonprofit supporting families affected by childhood cancer.
The Ruck March began five years ago when traditional fundraisers were impossible. Determined to keep supporting Why Me, Cinch I.T. founder Rick Porter and his team launched a military-inspired challenge: 100 miles, 40-pound packs, and four grueling days across Central Massachusetts.
Today, the Ruck March has grown into a beloved regional event, drawing 50 athletes each summer to hike 25 miles a day while carrying all they need on their backs: food, gear, and grit. Nights are spent camping out at local breweries like Stone Cow Brewery in Barre, where camaraderie, exhaustion, and determination come together under the stars.
100 Mile Ruck March starting line
The Spirit of The 100 Mile Ruck March
The Ruck March is not for the faint of heart. Each participant must carry their own pack, cook their own meals, set up and break down camp, and tend to injuries all while hiking 25 miles a day through unpredictable terrain and weather. But for many, that challenge is what makes the event so meaningful. “Every year I say it’s my last one,” laughed one returning athlete, “and then I see the Why Me families at the finish line, and I know I’ll be back next year.”
That finish line (often filled with cheers, tears, and hugs) has become a defining image of what the Ruck March represents: ordinary people doing something extraordinary for others. But this year’s march wasn’t just another lap around the course; it marked a milestone.
The 100 Mile Ruck March Course
The Five-Year Finishers Challenge
To celebrate five years of the Ruck March, Cinch I.T. introduced a special 5-Year Finishers Challenge, open only to past finishers willing to push themselves even further. The twist? The total mileage was undisclosed. Participants faced mental and physical obstacles throughout the course, navigating unknown distances while carrying everything they needed to survive for four days. “This challenge is about perseverance,” said event founder Rick Porter. “Every step represents what families fighting childhood cancer go through: the unknown, the exhaustion, and the drive to keep going further.”
Over the past five years, more than 150 athletes have taken on the 100 Mile Ruck March, raising tens of thousands of dollars for Why Me & Sherry’s House. Founded in 1985, Why Me & Sherry’s House was created from the vision of 13-year-old Sherry Shepherd, who dreamed of helping other children facing cancer. The organization continues that legacy today, offering emotional, financial, and community support to families from diagnosis through every stage of treatment and beyond.
“All 100% of the funds raised go directly to Why Me,” Porter emphasized. “They don’t receive government funding, so everything they do comes from the generosity of people right here in our community.” The Ruck March has become more than a fundraiser, it’s a symbol of hope, resilience, and unity.
Among the most heartwarming additions in recent years is the Kids Ruck, a pint-sized version of the adult challenge that invites young athletes, ages 6 to 18, to take part. The Kids Ruck takes place at Seven Saws Brewery, where participants set up tents with their parents, roast marshmallows by the fire, and wake at dawn to tackle as many one-mile loops as they can before the final cowbell rings.
“Watching a child lace up their boots, push through fatigue, and smile knowing they’re helping other kids, that’s what it’s all about,” said Porter. Each young participant earns their own finisher medal and Kids Ruck t-shirt, a proud symbol of their effort and compassion.
Rucker setting up his tent for the night
The Upcoming Documentary
While the physical march has wrapped up for the year, the story of the 2025 Ruck March is far from over. This December, Cinch I.T. will debut its fifth annual Ruck March Documentary, chronicling the emotional journey of this year’s athletes from the starting line to the final mile.
Produced and directed by Brandon Dziokonski, one of Cinch I.T.’s own, the film captures the raw, unfiltered moments that define the Ruck: the blistered feet, the quiet campfire conversations, and the powerful sense of purpose that drives every step.
“This documentary isn’t just about the miles,” said Brandon. “It’s about the people. Every Rucker comes with a story. Some have lost loved ones to cancer, some are veterans searching for connection, and others are just people who want to make a difference. When you see them out there, carrying everything on their backs, it changes the way you see endurance.”
The film, which premieres this December, offers the community a front-row seat to the heart of the Ruck, the exhaustion, the triumph, and the unbreakable spirit behind every mile. “This film is a celebration,” said Brandon. “It’s a thank-you to everyone who’s ever laced up, volunteered, donated, or cheered from the sidelines. It’s a reminder that when people come together for a cause, they can move mountains or, in our case, ruck 100 miles.”
The 100 Mile Ruck March Documentary Premiere will be held in December, with event details to be announced soon on Cinch I.T.’s social media pages. As Worcester residents mark their calendars, Porter hopes the story continues to spread far beyond Central Massachusetts. “We started this as a way to help one organization during a tough time,” he reflected. “Now, it’s become a movement. Five years later, the Ruck is still carrying that message that together, we can shoulder any weight.”
100 Mile Ruck March
More Information
For more information about the 100 Mile Ruck March and the upcoming documentary premiere, follow Cinch I.T. on social media for updates. Or visit elm draft houses social media where the Documentary will be featured.
To learn more about Why Me & Sherry’s House, visit www.whyme.org
To learn more about Cinch I.T. and how your company can get Fast & Friendly managed IT Services, visit https://cinchit.com/
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