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United States
Wisconsin
Calumet County

Sherwood

The best road cycling routes around Sherwood

4.5

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Road cycling routes around Sherwood traverse a landscape characterized by river valleys, parkland, and gentle elevations. The region offers varied terrain suitable for road cyclists seeking routes with moderate climbs and scenic stretches. Roads often follow waterways and pass through areas with open views and established park areas. The elevation changes are generally modest, making it accessible for a range of abilities.

Best road cycling routes around Sherwood

  • The most popular road cycling route is Guyette's – High Cliff State…

Last updated: November 1, 2026

4.0

(1)

7

riders

#1.

Guyette's – High Cliff State Park loop from Darboy

38.8km

01:38

140m

140m

Easy road ride. Mostly well-paved surfaces and easy to ride.

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Easy

Easy road ride. Mostly well-paved surfaces and easy to ride.

Easy
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Easy road ride. Mostly well-paved surfaces and easy to ride.

Easy

Moderate road ride. Good fitness required. Some segments of this route may be unpaved and difficult to ride.

Moderate

Easy road ride. Mostly well-paved surfaces and easy to ride.

Easy

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Popular around Sherwood

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Tips from the Community

JMB
June 27, 2025, Guyette's

Good food and nice owner

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The crossing was finished in 2021, and is open to foot and bicycle traffic over the Fox River. There is a little platform at the halfway mark from which you can pull off the main path and enjoy the views.

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A simple repair station by the water with a mount and pump. Great scenery, nice place to have a breakdown.

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In the pre-statehood era of Wisconsin, the Fox River was important to native tribes, travelers, and fur traders. Since 1760, a trading post has stood here. Charles A. Grignon built this home in 1837. Charles was an interpreter for the U.S. government during the Treaty of the Cedars. Today, the mansion can be seen from the street, can be entered for under 10 dollars, or a private tour can be taken.

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The Nelson Family Heritage Crossing is a recent addition to the city of Appleton, officially opening on June 18, 2021. This 1,100-foot bicycle and pedestrian bridge is an important car-free link, running from Heesakker Park in the Village of Little Chute and a new rail trail connection to Downtown Kaukauna.

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The Little Chute Windmill is a tribute to the Dutch heritage in the area. This functioning windmill site also offers the Van Asten Visitor Center and interpretive center in Little Chute. The building can be viewed from the street at any time, but the hours to visit the inside area are: Sunday, Monday, and Tuesday are closed. Wednesday, Thursday, Friday, and Saturday: 12:30 p.m.–4 p.m.

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Maple Syrup, Eggs, Honey

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Amy
October 7, 2022, Fox River

The Fox River flows 202 miles (325 km) from the Halbach Swamp in Wisconsin to the Illinois River, passing lots of towns and communities on its way. You can bike or hike easily along its banks thanks to the Fox River Trail.

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Frequently Asked Questions

What is the general terrain like for road cycling in Sherwood?

The Sherwood region offers a landscape characterized by river valleys, parkland, and gentle elevations. Road cycling routes typically feature moderate climbs and scenic stretches, often following waterways and passing through areas with open views. The elevation changes are generally modest, making it accessible for a range of abilities.

Are there road cycling routes suitable for beginners in Sherwood?

Yes, Sherwood is well-suited for beginners. Most of the routes are classified as easy, featuring gentle gradients. For example, the Guyette's – High Cliff State Park loop from Darboy is an easy 24.1-mile route through parkland, and the Little Chute Windmill – Fox River loop from Kimberly is another easy option offering scenic river views.

Are the road cycling routes in Sherwood typically circular?

Yes, the road cycling routes in Sherwood are predominantly circular, allowing you to start and finish at the same point. This makes planning your ride and parking more convenient.

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

Many routes offer scenic views and pass by interesting landmarks. You might encounter the historic Nelson Crossing, cycle near the expansive High Cliff State Park, or enjoy views of the Fox River and Lake Winnebago. The Little Chute Windmill – Fox River loop from Kimberly specifically passes by the Little Chute Windmill.

What is the best time of year to go road cycling in Sherwood?

The region's gentle terrain and scenic parklands are enjoyable throughout the warmer months, typically from spring through autumn. During these seasons, you can expect pleasant weather for cycling and lush natural surroundings. Winter cycling is possible, but conditions may vary, and some roads might be less maintained.

How long do road cycling routes in Sherwood typically take to complete?

The duration varies depending on the route and your pace. For instance, the Guyette's – High Cliff State Park loop from Darboy, which is 24.1 miles, typically takes about 1 hour 38 minutes. A slightly longer route like the Nelson Crossing Bridge – Fox River loop from Darboy (21.3 miles) might take around 1 hour 58 minutes due to its moderate difficulty.

Are there any moderately challenging road cycling routes in Sherwood?

While many routes are easy, there are options for those seeking a bit more challenge. The Nelson Crossing Bridge – Fox River loop from Darboy is classified as moderate, offering a 21.3-mile ride through river valleys and open countryside with slightly more elevation gain compared to the easier routes.

What do other road cyclists say about cycling in Sherwood?

The road cycling routes in Sherwood are highly rated by the komoot community, with an average score of 4.5 stars from over 10 reviews. Cyclists often praise the varied terrain, scenic views of the Fox River, and the accessibility of the routes through parkland and gentle hills.

Where can I find parking for road cycling routes in Sherwood?

Many routes start from towns or parks that offer parking facilities. For example, routes originating from Darboy or Kimberly, such as the Guyette's – High Cliff State Park loop from Darboy, typically have convenient starting points with parking options available in those areas or nearby state parks.

Are there any less-trafficked or 'hidden gem' routes for road cycling in Sherwood?

For a slightly different experience, consider the Guyette's – High Cliff State Park loop from Village of Harrison. This 31.1-mile easy route offers similar scenic beauty to other popular loops but might provide a quieter ride, allowing you to enjoy the parkland and river valley landscapes at a more relaxed pace.

Can I combine road cycling with other activities in Sherwood?

Absolutely. Given the proximity to natural attractions like High Cliff State Park and the Fox River, you can easily integrate short walks, picnics, or simply enjoy the natural surroundings before or after your ride. The Fox River State Trail also offers opportunities for multi-sport activities.

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