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Cup Chasers

Spread across five locations from the mountains to the Piedmont, the Commonwealth Cup race series brings together a range of riders from the Virginia mountain bike scene, including world-class athletes and weekend warriors. But on these rugged courses, the vibe is camaraderie over competitive edge.

Dennis Dempsey’s body is broken, but he can’t stay away from Virginia singletrack. Once a competitive mountain bike racer, Dempsey, who works at a D.C. think tank, now deals with the aftereffects of a cervical spine injury, which initially resulted in him losing the use of most of the right side of his body. Surgeries have helped, but he’ll never be 100 percent again.

With his time in the saddle limited, he decided to channel his love of the sport into a new pursuit—organizing races. 

 “I can go like a bandit for 45 minutes, but I’m never going to compete at Cat 1 the way I used to,” Dempsey said in the staccato accent of his native Philadelphia. “This is my way of staying involved.”

And stay involved he has. Earlier this year, Dempsey started the Commonwealth Cup, a series of five races running May through July that showcases some of the best mountain biking in Virginia, including the Western Slope of Massanutten, the winding foothills of Goochland County, and extensive trail systems at Douthat State Park, which holds a designated IMBA Epic Ride.  

Under the umbrella of RVA Racing, and with the help of longtime riders Kyle Inman and Chris Scott, Dempsey put together the series to help unify the Virginia mountain bike scene. He’s pulled in some old school classic races, including the Massunutten Hoo-Ha, with newer events like the Rockabilly Rumble in Palmyra.

In just its first year, almost 350 riders lined up for races in the Commonwealth Cup series, with fields that included sponsored juniors, NICA all-stars, 20-something beginners, and Cat 1 masters. 

As the series progressed, the races became more than competitions; they were community events where old friends reunited and friendly rivalries were established. Donuts were shared on podiums and series winners were crowned. 

Dennis Dempsey gets riders in the Commonwealth Cup ready to race. Photo courtesy of Dempsey

Dempsey has seen fierce rivalries turn into hugs at the finish line and watched teams share nutrition and even at least one full bike. 

The Cup’s community is a fun Breakfast Club of mountain bikers—a grassroots group of moms, dads, unicyclists, teachers, kids, self-proclaimed weirdos, and desk-strapped professionals. And if Demspey can’t be out there riding himself, bringing this group together is the next best thing.

“From the starting line to the finish line, everyone’s rooting for you, even if they’re competing with you,” he said. 

The Teacher

Sydney Wenger, a Dirt Camp Racing rider and Bike Flights ambassador, started the series by winning the Expert Women’s race at Middle Mountain Momma at Douthat State Park. 

Based out of Roanoke, Wenger is a teacher who’s been on a bike her whole life but didn’t start competing until she got burned out on competitive swimming.

Wenger, who races at the UCI level, was anxious at the start line of Middle Mountain Momma (MMM), which can be a grueling affair. The course is 18 miles (or 20 depending on what map you look at) and climbs 4,000 feet. Most cyclists consider 100 feet per mile a challenging ride. Paying to race 200 feet per mile takes a special kind of rider. 

The trails in Douthat State Park, one of the first six original Virginia state parks, only add to the difficulty. Most of them were cut by hand during the Depression by the Civilian Conservation Corps. They’re tight, rocky, and wind under rhododendron tunnels. These aren’t the manicured dirt highways you may see folks ripping on Youtube. MMM runs on proper backwoods trails.

“I’d done the race one time before. I’m incredibly directionally challenged and I messed up the course, so I was nervous going into it this time,” Wenger said. There was little need for concern, as Wenger nailed her nutrition strategy and took the win.

That racers of Wenger’s caliber come out for a local affair is a testament to the quality of events in the Blue Ridge. But it’s also the people who motivate Wenger to show up.

She appreciates the way cyclists in the region look out for each other and host events like a Thanksgiving ride to source food for those in need. Biking friends also helped get her through the brutal Chamois Shredder route after a couple attempts. 

“It’s a great community here,” she said. “I feel like everyone here is so welcoming.” 

The Local Legend

Jeremiah Bishop’s resume is extensive and impressive: two-time US National Champion, Alpine Grand Loop Fondo founder, Pan American gold medal winner, Canyon ambassador, co-founder of the Impossible Routes. 

He’s also the 2023 winner of the Pro/Expert race at the Massunutten Hoo-Ha, one of the longest running races, now in the state in its 34th year. The Hoo-Ha is held on the Western Slope of Massanutten, a fun playground for mountain bikers. The trails on the Western Slope start nice and easy at the bottom of the hill. At the top of the mountain they’re chunky and gnarly and with epic rock features and punchy descents that pull the standard “yew” noise of joy out of bikers as they fly down them. 

Bishop has plenty of wins at high-profile national events, but he always makes time to support local races and he’s clear about what keeps him coming out. 

“I think it’s the community really,” he said, noting the long and deep history of some of the races in the Commonwealth Cup. “It’s the longest collection of races running in the country with several of them being 35 years plus running.” 

Bishop sees the commitment of regional riders and the web of trail networks built with care and passion as the defining feature of the Blue Ridge.

“There’s an unspoken agreement that you help build and keep the trails in good shape, and keep the trails in good order,” he said. “Our scene is grassroots and it’s very much activity-based. We have some of the most fun trails, races, and rides in the country.”

The Mechanic

Micah Jewell likes to go fast. He lined up for every race of the Commonwealth Cup this year for Pedal Power RVA, the shop where he works as a mechanic. He spends his Tuesday nights racing crits for Car6on Racing, a team based out of Richmond dedicated to bringing more diversity to the sport. 

Jewell is just 22 and seems to know everyone at the races. To the juniors he’s the fast Cat 1 guy who knows everything about bikes. To the masters he’s very much the faster little brother whose maturity belies his age (most of the time; he does have a penchant for terrible jokes and bristles when middle-aged men use Gen Z slang).

His mom was the motivating force behind him getting on a bike. “I started mountain biking because my mom wanted us to do something outside together instead of me being inside playing video games,” he said. “So we all got bikes and started riding at Pocahontas State Park.”

Jewell won the Expert open category in the series and said there’s a lot to like about the cup. 

“We’re doing some of the biggest races in the state of Virginia,” he added. “The courses are all amazing. They’re tailored to different riding styles whether you like classic XC trails or chunky rocky stuff.”

The Coach and Course Designer

The course at Rockabilly Rumble, the last race of the Commonwealth Cup that ran in July, is special to John Petrylak. Not only because the race was on his local trails at Pleasant Grove Park, but also because he designed the course.

“I was able to put together a good mix of fun, fast, and challenging trails,” he said. “It’s gotta be fun for the person that this is their first race and for the person that it’s their hundredth.”

Petrylak knows the racers in Virginia well since he coaches many of them through the J. Petrylak Coaching Academy. 

“The people that race mountain bikes in Virginia are really the best part. We’re a big family. We always stop and help each other out. We’re there to support each other. We’re there to challenge each other. We’ll hurt you on the race course, but we’ll hug ya at the end.” 

You can learn more about the series and register for next year’s races at

Cover photo: Commonwealth Cup racer Micah Jewell. Photo Courtesy of Dennis Dempsey.

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