Defining the Trailhead
This dispatch was interpreted from Community Engagement & Programs Manager Marty Caivano's report of the event.
Stand on the ridges of the Skyline Wilderness Area and you’re treated to a striking duality: rugged, pine-covered hillsides that feel entirely wild, yet sit right within the city limits of Rapid City, South Dakota. It is a prized backyard asset, but like many heavily loved urban trail systems, it faces a constant battle against the elements.
In mid-May 2026, the Black Hills Bike Hub (BHBH) partnered with Rapid City Parks and Recreation staff to tackle a fundamental truth of trail stewardship: proper drainage doesn't have to ruin a ride—it can actually make it better. Insert: an IMBA Trail Care Workshop.
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Trail building, however, is often a matter of perspective. Kevin Leoffler, the passionate head of trails for Rapid City Parks & Rec, is an avid trail runner. He views the landscape through the lens of shedding water as efficiently as possible. Without a rider's perspective, he had been installing drains in places that inadvertently disrupted the flow of the trail, breaking the critical support of insloped turns. Meanwhile, an eager crew of local volunteers had yet to experience the magic of the "basin and rise" technique—a method that uses gentle slopes and flat areas to create larger, rolling shapes that simultaneously manage water and maximize fun.
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Over the course of the weekend, everyone dug in. Divided across four critical zones that desperately needed love, the crew traded theories for dirt on their shovels. The energy was infectious, with classroom and trailside education sessions led by IMBA Trail Solutions' Joey Klein, Cory Callahan, and Marty Caivano. Joey even connected with a local freeride and dirt jump enthusiast in the group, quickly befriending him to help channel his passion for shaping dirt into sustainable, sanctioned local features.
The real magic of these workshops, though, happens in the shift in perspective. Near the end of a grueling workday, a local rider coasted through the freshly reworked section. Her immediate, unbridled excitement over the improvements became the ultimate proof of concept—especially for Kevin. Seeing a rider light up over a drainage fix completely blew him away. The transformation trickled down, too; one city staff member approached Joey and Marty afterward, entirely converted and asking when he could take the next available advanced clinic.
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As Evan Walterman of BHBH later noted, bridging that gap with land managers changes everything. "That insight will make all the difference both in how Kevin works, but also how he will be set up for success to have that work well-received by trail users," Evan shared. "Positions like his can be difficult when we have a highly engaged and vocal membership, but we are in a great place to build a foundation of trust and collaboration."
That trust is already radiating beyond the city limits. Word travels fast when a community aligns, and land managers from the nearby Buffalo Gap National Grasslands have already reached out to BHBH for guidance on a brand-new trail development. Joey swung by the grasslands on his way out of town to read the terrain, leaving Emily Berry of BHBH with a list of strategic observations to steer their upcoming planning meetings.
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Between the sweat on the trail, the breakthrough conversations, and a handful of incredible evening rides experiencing Rapid City's local culture, the verdict is a resounding A++. This crew deeply embodies the community-focused style of advocacy we love to see, proving their IMBA Trail Town status is earned a shovelful at a time. Skyline already has more workdays on the books to keep the momentum moving—go team!
Interested in scheduling with our crew? Learn more:
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