Going the Distance

On any given morning as you’re out and about in Chester County, you might spot two familiar figures moving through the countryside: one running the wooded trails of a local nature preserve, the other pedaling miles of winding country roads.

This is just an ordinary day for brothers Stephen and Stewart Gross, for whom training for their ultra-endurance sports is both routine and a passion. These activities are a way of life that dates back to childhood and now persists decades later as they managed to continue putting in the miles despite demanding careers in real estate and growing families.

Business and Training

Both brothers now work with the family business, Holly Gross Group, an established real estate firm with over four decades of experience in the Brandywine Valley and beyond. The firm has served the area since the 1980s and is known for helping buyers and sellers navigate the region’s competitive market with comprehensive, personal service.

For the Gross brothers, returning home to Chester County after years of exploring the world and other pursuits — Stephen working in Europe and Asia, Stewart living the Colorado dream of snowboarding and professional mountain biking — it’s the perfect fit.

They have been involved in several hundred million dollars of real estate transactions, earning reputations for persistence and professionalism in a demanding, fast-paced and often unpredictable, around-the-clock environment. Yet both have also built remarkable resumes in endurance sports, integrating their training with their work.

“It’s a 24/7 job,” Stewart said of real estate. “Before a 100-mile bike race, I was writing an agreement of sale at 12:30 in the morning, knowing I had to be up in four hours. You’re always in the game.” Stephen added, “I remember pausing on a mountaintop during a race to respond to a business text for a negotiation.”

Roots in Chester County

Their story begins in the heart of Chester County, where the brothers were surrounded by the landscapes that still define their training today. “We grew up in Unionville,” Stephen said. “Our parents had a horse farm that backs up to The Laurels Preserve — over 900 acres of protected land. We had mountain bikes from a young age and raced around Chester County and southeastern Pennsylvania.”

Like many local kids, their days were filled with sports and time outdoors. At Upland Country Day School, both brothers were three-sport athletes. “Sports were always part of our lives,” said Stephen, who pointed out that although he got the school’s athletic award, it was younger brother Stewart who was one of the school’s only professional athletes.

Early years cycling on dirt trails and running on footpaths across the county built the foundation for what came later: a lifelong appetite for challenge and distance. Today, the same landscape still plays a central role in their training routines. Stephen frequently runs through conserved lands that dot the county — such as The Laurels and ChesLen Preserves, both part of the vast network of protected open spaces that make our area such a remarkable place to live, exercise and enjoy the outdoors. “The great thing about Chester County is the access to open land,” Stephen said. “You can be on trails in minutes.”

Pushing Limits on Foot

While Stewart ultimately focused on ultra-distance cycling, Stephen found his calling in ultramarathon running. Since completing his first ultra-race along the Susquehanna in 2015, he’s finished more than a dozen races around the world, from rugged trail marathons to 15 ultramarathon courses in the U.S., Europe and Canada. His best performances include winning the Cloudsplitter 100k in Norton, Virginia and 10th place in the 100k Quebec Mega Trail.

But perhaps his most impressive accomplishment, to date, came in 2025 when he completed the legendary Ultra Trail du Mont Blanc (known as the Super Bowl of trail running). The race begins in Chamonix, France, then heads to Italy and Switzerland — a grueling 110-mile challenge with roughly 30,000 feet of climbing.

For most runners, simply finishing is the goal. But for Stephen, the deeper motivation is something more personal. “Ultra-running really self-selects for people who can endure suffering, who somehow get enjoyment from doing hard things for a long time.” Part of that drive comes from the emotional rewards that follow the physical effort. “After the Quebec Mega Trail race, I had a runner’s high for an entire week. I was on cloud nine,” he said.

The Endurance Cyclist

Not a fan of running, Stewart took a different route, leading him deep into the world of ultra-endurance cycling. After graduating from college in 2006, he entered a 100-mile mountain bike race called the Wilderness 101 close to State College. “I had no idea what I was doing, but I found a group playing reggae music and tried to keep up” said Stewart, who finished this first race in 14.5 hours. “I loved it! Especially the last 20 miles.”

That experience launched a long career in endurance racing, which admittedly included some “trials by failure” but ultimately led to an inspiring history of success.

Over the years, Stewart has competed in some of North America’s toughest mountain bike events and earned national rankings in the National Ultra Endurance Series as recently as 2025 whe he placed 5th overall. His results include multiple top-5 finishes in 100-mile mountain bike races and victories in ultra-distance gravel race events, including the fastest known time for the 385-mile Crush the Commonwealth race (Philadelphia to Pittsburgh).

When he repeated his first ultra-distance race course, the Wilderness 101 in 2015, he cut his original time in half and finished 10th overall that year, 5th overall the next year, and 5th in 2025 when he was the oldest rider on the podium by 11 years.

Even after racing professionally, his training still revolves around well-loved roads of Chester County. Now, in addition to racing, Stewart can be found supporting the sport that’s given him such a strong sense of identity. He’s race director for a mountain bike race in French Creek State Park, coaches and sponsors the West Chester high school mountain bike team, and the family business, Holly Gross Group, is also involved and sponsors several local events, including the local race series, the Mid-Atlantic Super Series (MASS).

The Mental Game

For both brothers, the real challenge of endurance sports isn’t mere physical strength. It’s mental resilience. “My legs cramp up so many times that they can no longer argue with me,” Stewart said of long races. That mindset has proven surprisingly useful in their professional lives as well.

“Real estate can be tough,” added Stephen. “It’s often a long slog, just like these races. The mindset you build from endurance sports carries over.” Negotiations can take longer than expected, with unanticipated variables to derail a deal. The persistence required in ultra-distance racing — continuing mile after mile when fatigue sets in — turns out to be excellent preparation for long-term deal making. “It’s probably 50% mental, 50% physical,” Stewart said. “We both definitely have that mental capability to endure.”

Balance in Motion

Another impressive aspect of the Gross brothers’ story is their ability to balance their ultra-endurance sports and demanding professional careers with family life. Both brothers emphasize that discipline plus their family support make everything possible.

“Training goes on the calendar like an appointment,” Stewart said. “but you still have to be willing to skip a race if your family or clients need you.” Stephen takes a similar approach, fitting runs around a constantly changing real estate schedule. “Family comes first,” he said. “Then work. Then training.”

What do their parents, Holly and Dick Gross, think about their sons’ sports? “Sometimes they think we’re total freaks and don’t know why we do it. But they’re also so proud of us. And we’re always happy to have them at the races, along with the rest of our families,” Stewart said.

A County That Inspires

That work-life-sports balance may be easier in a place like Chester County, where the environment invites exploration and enjoyment. From wooded preserves to quiet back roads, our region offers endless opportunities to get outside.

So while you’re outside on local roads and trails this spring, watch out for Stephen and Stewart as the brothers prepare for their 2026 races. As Stephen put it, “For some people, this kind of endurance sport just clicks. Once it does, it becomes part of who you are.”

In Chester County, they’ve found the perfect place to keep going the distance.

If you’re inspired by the Gross brothers’ example, some places to start your journey include The Laurels, Stroud and ChesLen Preserves, Marsh Creek State Park, Valley Forge National Historic Park, scenic paths throughout the Brandywine Valley and countless country roads.

Zack Malet is County Lines’ occasional sports columnist and former Brown University Track Team member, who after completing the Philly half-marathon vowed he’d never race farther. But after interviewing the Gross brothers, he’s reconsidering.