5.0
(7)
108
riders
17
rides
Road cycling around Sheboygan offers a diverse landscape for riders, characterized by its Lake Michigan shoreline and extensive network of multi-use trails. The region features glacial hills and rolling countryside to the west, along with open farmlands, quiet woodlands, and sweeping prairies. Sheboygan County provides varied terrain, from flat coastal paths to routes with over 1,000 feet of elevation gain, catering to different road cycling preferences.
Last updated: July 21, 2026
6
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.
1
riders
66.1km
02:44
310m
310m
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.
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Popular around Sheboygan
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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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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Fischer Creek Conservation Area is the newest addition to the Manitowoc County Park System. This 160-acre site is owned by the state and maintained by the county. The area offers peaceful beach access, hiking trails, and viewpoints perfect to enjoy during all four seasons.
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Great coffee, great food, and great staff. The cafe is well presented and clean as well. And if you have a wedding, party, or other event coming up they can cover that too!
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Hingham Mill Pond is a small (38 acre) and shallow (6 feet maximum depth) pond in Hingham, Wisconsin. It's known among anglers as a place to catch panfish and Northern Pike.
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Sheboygan offers a diverse selection of over 15 road cycling routes. These routes cater to various skill levels, with 6 easy, 10 moderate, and 1 difficult option, ensuring there's a suitable ride for every cyclist.
Road cycling routes in Sheboygan showcase a rich variety of landscapes. You'll find stunning views along the Lake Michigan shoreline, the towering sand dunes and pine forests of Kohler-Andrae State Park, and the glacial hills and rolling countryside of the Kettle Moraine State Forest. Many routes also pass through open farmlands, quiet woodlands, and sweeping prairies, offering a truly diverse experience.
Yes, Sheboygan has several easy road cycling options suitable for families. Trails like the Shoreland 400 Rail Trail and the Taylor Drive Pathway offer paved, multi-use surfaces within the city. For a slightly longer, yet still accessible ride, parts of the Old Plank Road Trail provide gentle terrain through varied scenery.
Many routes offer opportunities to see local landmarks and natural attractions. You can cycle past the beautiful Kohler-Andrae State Park, enjoy views of the Sheboygan Breakwater Lighthouse, or even visit Sheboygan Falls. The Kettle Moraine State Forest, accessible via routes like the Sheboygan to Elkhart Lake loop, also features the Parnell Observation Tower with panoramic views.
Yes, many of Sheboygan's road cycling routes are designed as loops, allowing you to start and end at the same point. Examples include the Sheboygan Interurban and Old Plank Road Trail Loop, the Sheboygan to Fischer Creek State Recreation Area loop, and the longer Sheboygan century loop.
Sheboygan offers varied terrain. Along the Lake Michigan shoreline, you'll find flatter coastal paths. Heading west, routes transition into the glacial hills and rolling countryside of the Kettle Moraine, with some routes featuring over 1,000 feet of elevation gain, such as the Sheboygan to Elkhart Lake loop. You'll also encounter open farmlands and quiet woodlands.
The area is highly rated by the komoot community, with an average score of 4.5 stars. Reviewers often praise the diverse scenery, from Lake Michigan views to rural Wisconsin countryside, and the extensive network of well-maintained multi-use trails that cater to various preferences.
While many local trails are free to use, some state parks and trails, such as those within Kohler-Andrae State Park, may require a Wisconsin State Park System vehicle admission sticker or a trail pass. It's advisable to check the specific requirements for the trails you plan to ride. More information on local trails can often be found on the Visit Sheboygan website.
The spring, summer, and fall months generally offer the most pleasant conditions for road biking in Sheboygan. Spring brings blooming landscapes, summer provides warm weather for lakeside rides, and fall showcases beautiful foliage, especially in areas like the Kettle Moraine State Forest. Winter can be challenging due to snow and ice, making many trails less suitable for road bikes.
Parking is generally available at various trailheads and parks throughout Sheboygan. For instance, Kohler-Andrae State Park offers parking for access to its trails. Within the city, many public parks and access points to trails like the Shoreland 400 Rail Trail or Taylor Drive Pathway provide parking facilities. It's recommended to check specific starting points for parking availability.
Sheboygan's public transport system, Shoreline Metro, offers routes throughout the city. While buses may not directly access all trailheads, they can get you close to many urban trails and starting points. Cyclists should check the bus routes and policies regarding bikes on board for specific planning.
Yes, advanced road cyclists can find challenging routes in Sheboygan. The Sheboygan century loop, for example, is classified as difficult, covering a significant distance with notable elevation changes. Routes venturing into the Kettle Moraine State Forest also tend to offer more demanding climbs and longer distances.
Many routes, especially those passing through or near Sheboygan's urban areas and smaller towns like Elkhart Lake, offer opportunities to stop at cafes, pubs, or restaurants. The city of Sheboygan itself has numerous establishments. For routes venturing into more rural areas, it's wise to plan your stops in advance or carry sufficient supplies.


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