Cycling & running events in Sheboygan, 2026

Sheboygan Training Notes

Running: Locals run Sheboygan by stitching lakefront miles to the Old Plank Road Trail. The Old Plank Road Trail runs roughly 21 miles west from the Kohler Erie Avenue Trailhead, and it is the easy call for base miles or a steady Z2 out-and-back. The Shoreland 400 Rail Trail runs less than 2 miles from Vollrath Park, and it mostly runs along the lake, so it stays cooler. Keyon Tinnon used a north-side-to-lakefront line past Blue Harbor Resort while chasing every city street. Sheboygan County Shoreline Striders Running Club keeps the scene social on weeknights and weekends. Acuity Neonatal Run/Walk, Sheboygan YMCA Freedom Run with myTEAM TRIUMPH, and Old Plank Sunset Half Marathon give the calendar its anchor races.

Cycling: Locals ride the same coastal grid, then point west when the legs need work. The Old Plank Road Trail carries cyclists toward Greenbush, where the terrain turns from flat to gently rolling and throws one large climb or descent near County Highway S just east of Greenbush. The Lakefront Bike Path begins off Indiana Avenue and connects to the Pier Boardwalk for an easy spin by Lake Michigan. Evergreen Park biking trails connect with Maywood and Quarry Park, and that pocket feels like North Woods riding even while it sits right in town. Sheboygan County Cycling maintains mountain bike trails, builds new ones, runs group rides, and hosts the SCC Classic Cyclocross Race at Quarry Park. The Eisenbahn State Trail, Sheboygan Interurban trail, and Eisenbahn and Bug Line work for longer dirt rails-to-trails days.

Season: Spring, summer, and fall are the clean training months here. Lake Michigan keeps summer runs cooler along the shore, and evening races can bring bugs and mosquitos, so locals plan intervals and long runs with that in mind. Sheboygan carries that coastal oddity too, because the city is the Malibu of the Midwest and once hosted the Dairyland Surf Classic from 1988 to 2012. Winter changes the rhythm for both sports. Runners stay closer to paved paths and town loops, while cyclists lean into fat tires, indoor work, or snow-season access where the Black River Trail in Kohler-Andrae allows snowmobilers.