4.4
(13)
180
riders
26
rides
Road cycling in Sheboygan County features a diverse landscape shaped by glacial activity, offering varied terrain for cyclists. The region is characterized by rolling hills, valleys, and extensive forests, including the Kettle Moraine State Forest. Its position along the Lake Michigan shoreline provides scenic waterfront routes. An impressive network of paved multi-use trails complements the rural roads, catering to different cycling preferences.
Last updated: April 24, 2026
9
riders
Moderate road ride. Good fitness required. Mostly well-paved surfaces and easy to ride.
2
riders
46.7km
02:08
160m
170m
Moderate road ride. Good fitness required. Mostly well-paved surfaces and easy to ride.

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2
riders
48.6km
02:04
130m
130m
Moderate road ride. Good fitness required. Mostly well-paved surfaces and easy to ride.
51.8km
02:25
340m
340m
Moderate road ride. Good fitness required. Mostly well-paved surfaces and easy to ride.
66.1km
02:44
310m
310m
Moderate road ride. Good fitness required. Mostly well-paved surfaces and easy to ride.
77.8km
03:25
350m
350m
Moderate road ride. Good fitness required. Mostly well-paved surfaces and easy to ride.
159km
07:15
510m
510m
Hard road ride. Very good fitness required. Mostly well-paved surfaces and easy to ride.
30
riders
45.9km
01:55
180m
180m
Easy road ride. Great for any fitness level. Mostly well-paved surfaces and easy to ride.
5.0
(2)
21
riders
60.5km
02:23
110m
110m
Moderate road ride. Good fitness required. Mostly well-paved surfaces and easy to ride.
21
riders
38.6km
01:33
150m
150m
Easy road ride. Great for any fitness level. Mostly well-paved surfaces and easy to ride.
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Popular around Sheboygan County
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Road Cycling Routes in Kettle Moraine State Forest

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Road Cycling Routes around Plymouth
The Ozaukee - Sheboygan Interurban Trail runs for 40 miles between Milwaukee and Sheboygan along the converted Milwaukee Electric Railway and Light Company interurban passenger railway. The trail passes through, or very near, many towns, villages, and state parks. Making it a wonderful way to explore the area on two wheels.
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Though it's less than 30 miles from Milwaukee, Port Washington has enough of its own character and charm to stand on its own. Along with the interesting architecture, great restaurants, and beautiful waterfront district, the town is host to a number of events throughout the year such as Port Fish Days and Music at the West Slip Beer Garden.
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The Cedar Grove Windmill is an ode to the Dutch heritage in the area. It was originally called the "De Visch" windmill and was built in 1968. It stands 28 feet tall as a scale model of the windmills found in Dutch cities.
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Nowack House is one of many historic structures in Random Lake. In fact the surrounding area has quite a few of these information plaques placed in important locations for those who spend the time to read them.
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Random is the name of both the lake, and the town that sits along its shore. The lake itself is 212 acres and popular for fishing year round. You can expect to find Largemouth Bass, Walleye, Musky, and Northern Pike.
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Evergreen is a large woodland park with miles of hiking and biking trails. It's bordered on 2 sides by other parks, making for a massive contiguous park area. In addition to the trails the parks also have picnic areas, playgrounds, a pond, and a disc golf course.
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Sheboygan County offers over 25 road cycling routes, catering to various preferences and skill levels. These include routes along the Lake Michigan shoreline, through the Kettle Moraine State Forest, and on an extensive network of paved multi-use trails.
The terrain in Sheboygan County is diverse, shaped by glacial activity. You'll find rolling hills and valleys, particularly within the Kettle Moraine State Forest, offering both challenging climbs and picturesque descents. Along the Lake Michigan shoreline, routes provide stunning waterfront views and refreshing breezes. Additionally, there's an impressive network of paved off-road multi-use trails, such as the Old Plank Road Trail and the Sheboygan Interurban Trail, which offer smoother, flatter sections.
Yes, Sheboygan County has several easy routes suitable for beginners. For example, the Old Plank Road Trail loop from Town of Sheboygan is an easy option. The Old Plank Road Trail itself offers a mix of flat and gently rolling terrain, making it accessible for those new to road cycling.
For longer and more challenging rides, consider routes that explore the rural Wisconsin scenery or venture deeper into the Kettle Moraine State Forest. The Sheboygan century loop is a difficult 99-mile route that provides diverse scenery and lake views. Another option is the Random Lake to Kettle Moraine State Forest loop, which offers a moderate challenge over a significant distance.
Many routes offer beautiful scenery. Along the Lake Michigan shoreline, you can enjoy continuous waterfront vistas, especially on routes near Kohler-Andrae State Park, which features unique sand dunes and beaches. Inland, the Kettle Moraine State Forest provides stunning views of glacial features, forests, and lakes like Elkhart Lake and Random Lake. You might also encounter the Parnell Observation Tower for panoramic views.
Yes, Sheboygan County features several excellent loop routes. A popular choice is the Sheboygan Interurban and Old Plank Road Trail Loop, which combines two key paved trails. Another great option is the Kettle Moraine Forest loop from Elkhart Lake, offering scenic views through the forest.
The spring, summer, and fall months generally offer the best conditions for road cycling in Sheboygan County. During these seasons, the weather is typically mild, and the natural landscapes are vibrant. While winter cycling is possible, be prepared for colder temperatures and potential snow or ice on trails and roads.
Dog policies vary by specific trail and park. For instance, Kohler-Andrae State Park, which the Sheboygan Interurban Trail passes through, generally allows leashed dogs on trails. It's always best to check the specific regulations for each trail or park you plan to visit, as rules can differ.
Many of the major trailheads and state parks offer designated parking areas. For example, the Old Plank Road Trail has parking available along its length, including in the Town of Sheboygan. State parks like Kohler-Andrae also provide parking facilities. Always look for official parking lots to ensure a safe and legal spot for your vehicle.
Yes, several routes pass through or near towns and communities where you can find cafes and other amenities. For instance, the Moxie Coffee Café & Catering – Old Plank Road Trail loop from Plymouth specifically highlights a cafe. Routes near Sheboygan, Elkhart Lake, and other towns will offer opportunities for refreshments.
The area is highly rated by the komoot community, with an average score of 4.3 stars. Reviewers often praise the diverse scenery, which includes stunning Lake Michigan views and the unique glacial landscape of the Kettle Moraine State Forest. The extensive network of well-maintained paved trails and quiet rural roads also receives high marks for providing varied and enjoyable cycling experiences.
Sheboygan Transit buses are equipped with bike racks, allowing cyclists to combine public transportation with their rides. This can be useful for reaching trailheads or extending your cycling range without needing to drive. For specific routes and schedules, it's advisable to check the Sheboygan Transit website directly.


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