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All photos courtesy of Carrie Kost and Sheboygan County CyclingSheboygan County, in southeastern Wisconsin, is a bit of a trail desert when it comes to mountain biking. While the area has plenty of road and gravel riding, trail systems allowing mountain bike access are few and far between.
“Even though we focus on all things cycling, the big needs were on the mountain bike side,” Brian Schwaller, President of Sheboygan County Cycling (SCC), told us. Initially, SCC looked to add trails at Evergreen Park, but ran into roadblocks. So, with the Evergreen project paused, the group turned to revamping an all-but-forgotten trail system around a medical center.

An opportunity at Rocky Knoll
Southeastern Wisconsin, and, more specifically, the Sheboygan area, has deep roots in cycling and racing. Road cycling, that is. Schwaller explained that the area used to host Superweek, one of the largest and most prestigious stage races in North America.
Road, cyclocross, and gravel: most of the cycling in Sheboygan County involves much skinnier tires. It wasn’t uncommon for mountain bikers in the area to travel multiple hours to get to trail systems, often heading north.
Hoping to create more local opportunities, SCC turned its attention to Evergreen Park, an established trail system just north of Sheboygan. In that instance, SCC was working with the City of Sheboygan, and the plan to expand the trail system ultimately encountered delays.
Knowing that the Evergreen Park trail expansion project was on hold, Sheboygan County asked SCC to focus its attention on another trail system near the town of Plymouth. The county-owned land around a medical center had some trails added years back, and they were perhaps due for a refresh.
But Schwaller and SCC felt like they might need a bit more than that.

Wait, there are trails at Rocky Knoll?…
“[Some locals were] saying that there are trails at Rocky Knoll, and I didn’t know,” Schwaller said. “And I’m a three-minute ride from my house to those trails.”
The Rocky Knoll trails then, and now, circle a medical center that sits atop a hill. Established in 1926, the medical center was originally a tuberculosis sanatorium, and has been some sort of medical facility for its 100-year history.
Today, it operates as a rehabilitation facility. As we’ll later see, some old and new trail names were medically inspired.
In 2019, Sheboygan County wanted to do something with the land that surrounds the Rocky Knoll Health Care Center. Fortunately, so did a Boy Scout group. A grant was provided for trails on the land around the medical center.


While the troop put in a valiant effort and, in many ways, laid a foundation at Rocky Knoll, the trails sadly fell into disrepair over the years.
When the county inquired about “fixing them up,” Schwaller couldn’t help but interject. If the goal were to have more than a few riders checking out the trails, the project would need to include more than just “fixing them up.” He mentioned that some of the trails were just crudely scraped into the ground, creating water channels and erosion. Many of the corners were too tight for a modern trail bike, and, somehow, nearly every tree along the trail was cut right at pedal-strike level.
To attract mountain bikers to come and ride at the Rocky Knoll Trail System, the area would essentially need a rebuild. And, if SCC could add a handful of new trails, that would be icing on the cake.
Fortunately, Sheboygan County was happy to oblige.

A refreshed trail system
“The Tuberculosis Trail, that’s the Boy Scout trail,” Schwaller explained. “That’s actually really cool. It’s just a fun tight little trail.”
Tuberculosis stretches over a mile and a half around Rocky Knoll and is a solid intermediate trail, although Schwaller mentioned it has spicy areas leaning into dark blue. Aside from more minor adjustments, SCC left this trail alone for the most part.
Another existing trail from the Boy Scout build was Old Yeller. This was the trail that was essentially scraped into the ground. The trail builder hired for the project, Dynamic Trailworx, regraded the Old Yeller trail, adding berms and whoops to create more flow.
Old Yeller is a much-needed green trail in the trail system. In fact, beginner trails were especially sparse in the county, as greens were practically nonexistent. In total, Rocky Knoll now boasts seven beginner-friendly trails, including “Vital Ascent” and “Road to Recovery.”
Tech and flow, and even a bit of woodwork, are well mixed into Rocky Knoll’s intermediate trails and skills area. Trails like “Bedpan” and “Medicine Bottle” can either be XC- or descending-focused.

With descending in mind, Rocky Knoll does have DH-only trails. “First Dose,” “Fresh Air,” and “Chicken Joe” are the system’s directional jump trails, with First Dose appropriately named as Rocky Knoll’s first entry into a jump line. Schwaller said that the advanced-rated Chicken Joe jump trail does feature gaps, while Rocky Knoll’s other black trail, Physical Therapy, leans more into the tech.
“Physical therapy is fun. You can go fast enough that you’re gonna scare yourself.”
In addition to the seven green trails, Rocky Knoll offers five blue and two black. There are roughly five miles of trails, with nearly 500 feet of elevation gain and descent, provided you ride them all. As you might expect for a Wisconsin trail system, Rocky Knoll is heavily forested, where rocks and roots are abundant.
Overall, the system leans toward fast-flow XC riding and provides a solid option for steady progression.
Fingers crossed for more
SCC and Schwaller couldn’t be happier to work with Sheboygan County on this project. And they also watched the community step up to fund the roughly $130,000 to rebuild Rocky Knoll. Moving forward, they anticipate that the success of the Rocky Knoll Trail System will reinvigorate projects like the Evergreen Park.
While Evergreen might be SCC’s next adventure, they hope it doesn’t stop there. Schwaller mentioned the proximity of the Kettle Moraine State Forest, which has 30,000 acres and very few bike trails.
The group hopes that success at their current projects opens doors in places like that.


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