4.5
(12)
47
riders
4
rides
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.
Last updated: November 1, 2026
4.0
(1)
7
riders
38.8km
01:38
140m
140m
Easy road ride. Mostly well-paved surfaces and easy to ride.
5.0
(1)
16
riders
43.1km
01:52
200m
200m
Easy road ride. Mostly well-paved surfaces and easy to ride.

4.7
(3)
13
riders
31.1km
01:23
130m
130m
Easy road ride. Mostly well-paved surfaces and easy to ride.
5.0
(6)
6
riders
34.2km
02:07
150m
150m
Moderate road ride. Good fitness required. Some segments of this route may be unpaved and difficult to ride.
4.0
(1)
3
riders
25.2km
01:08
100m
100m
Easy road ride. Mostly well-paved surfaces and easy to ride.
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Popular around Sherwood
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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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.
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.
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.
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.
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.
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.
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.
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.
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.
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.
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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