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Road cycling routes
United States
Wisconsin
Sheboygan County

Sheboygan

The best road cycling routes around Sheboygan

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.

Best road cycling routes around Sheboygan

  • The most popular road cycling route is Kohler-Andrae…

Last updated: July 21, 2026

6

riders

#1.

Kohler-Andrae State Park to Port Washington loop via the Ozaukee—Sheboygan Interurban Trail

81.5km

03:18

210m

210m

Moderate road ride. Good fitness required. Mostly well-paved surfaces and easy to ride.

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Moderate

Moderate road ride. Good fitness required. Mostly well-paved surfaces and easy to ride.

Moderate
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Moderate road ride. Good fitness required. Mostly well-paved surfaces and easy to ride.

Moderate

1

riders

Moderate road ride. Good fitness required. Mostly well-paved surfaces and easy to ride.

Moderate

159km

07:15

510m

510m

Hard road ride. Very good fitness required. Mostly well-paved surfaces and easy to ride.

Hard
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Popular around Sheboygan

Hiking around Sheboygan

Running Trails around Sheboygan

Tips from the Community

Grant Gehweiler
September 23, 2024, Kohler-Andrae State Park

Great sand beach with dunes.

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Great place to stop for a rest.

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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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Andrus
July 19, 2024, Port Washington

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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Andrus
July 19, 2024, Evergreen Park

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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Frequently Asked Questions

How many road cycling routes are available in Sheboygan, and what are their difficulty levels?

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.

What kind of natural features and scenic views can I expect on road cycling routes around Sheboygan?

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.

Are there any family-friendly road cycling routes in Sheboygan?

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.

What are some notable landmarks or attractions I can see along the road cycling routes?

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.

Are there any circular road cycling routes in the Sheboygan area?

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.

What is the terrain like for road cycling in Sheboygan?

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.

What do other road cyclists enjoy most about road cycling in Sheboygan?

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.

Are there any specific permits or fees required to use the bike trails in Sheboygan?

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.

What is the best season for road biking in Sheboygan?

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.

Where can I find parking near the road cycling trails in Sheboygan?

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.

Can I access Sheboygan's bike trails using public transport?

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.

Are there options for advanced road cyclists looking for a challenge?

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.

Are there any cafes or pubs along the road cycling routes in Sheboygan?

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.

Most popular routes around Sheboygan

Traffic-free bike rides around Sheboygan

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Sheboygan FallsKohlerKohler-Andrae State ParkOostburgElkhart LakeGibbsvilleKettle Moraine State ForestPlymouthGlenbeulahGreenbushHowards GroveCedar Grove

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