4.8
(14)
111
riders
19
rides
Road cycling routes in Winnebago County traverse a landscape characterized by rolling plains, extensive forest preserves, and scenic river valleys. The region features the Rock River and Kishwaukee River, along with lakes such as Pierce Lake and Olson Lake, providing varied backdrops for cycling. Over 11,000 acres of forest preserves offer a mix of prairies and woodlands. This topography provides diverse terrain for road cyclists.
Last updated: May 27, 2026
2
riders
80.9km
03:59
200m
200m
Cycle the Fox Cities Paper Trail, a 50.3-mile (80.9 km) moderate road cycling route through urban and natural scenery.
6
riders
19.1km
00:51
70m
70m
Cycle the easy 11.9-mile Little Chute loop near Appleton, offering Fox River views and a glimpse of the Appleton Swing Railroad Bridge.

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4
riders
28.1km
01:18
120m
120m
Enjoy an easy 17.5-mile road cycling loop on the Kaukauna loop, featuring scenic Fox River views and historic landmarks.
10
riders
16.3km
00:46
50m
50m
Easy road ride. Great for any fitness level. Mostly well-paved surfaces and easy to ride.
5
riders
32.1km
01:25
70m
70m
Easy road ride. Great for any fitness level. Mostly well-paved surfaces and easy to ride.
4
riders
26.2km
01:12
70m
70m
Easy road ride. Great for any fitness level. Mostly well-paved surfaces and easy to ride.
5.0
(1)
6
riders
17.2km
00:44
40m
40m
Easy road ride. Great for any fitness level. Mostly well-paved surfaces and easy to ride.
3
riders
Easy road ride. Great for any fitness level. Mostly well-paved surfaces and easy to ride.
3
riders
21.8km
00:55
50m
50m
Easy road ride. Great for any fitness level. Mostly well-paved surfaces and easy to ride.
3
riders
25.0km
01:05
60m
60m
Easy road ride. Great for any fitness level. Mostly well-paved surfaces and easy to ride.
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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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Hearthstone Historic House is sometimes called the birthplace of green energy because it was the first private house to be illuminated using hydroelectricity from a central Edison system. Take a tour and see the Edison electroliers, light switches, and more that still remain intact in the house. The home is on the National Register of Historic Places, and it is a great historical and educational stop.
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Grant Park is a small, 1.13-acre park with mowed grass and trees for shade. This area is along Little Lake Butte des Morts and provides nice views of the water and a shady spot to relax.
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The Friendship State Trail is 4 miles long, end to end, and goes through forests, farmland, and next to lakes. The trail connects the Fox River State Trail in Forest Junction and is carefully maintained and operated by Calumet County.
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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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This swing bridge is the last large through-truss bridge on the Fox River. It was constructed in 1929 on concrete and stone and is still in use today.
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Telulah Park spans 27 acres and boasts a large pavilion, restrooms, drinking fountains, a soccer field, tennis courts, basketball courts, skateboard and roller blade courts, ADA playground equipment, a ball diamond, 18-hole disc golf, and cross-country skiing in the winter. The park is open to the public every day from 5 a.m. to 11 p.m.
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Winnebago County offers a diverse selection of over 19 road cycling routes, catering to various skill levels. You'll find everything from easy, leisurely rides to more moderate challenges across the region's varied terrain.
Road cycling in Winnebago County features a mix of rolling plains, extensive forest preserves, and scenic river valleys. Routes often follow the Rock River and Kishwaukee River, providing picturesque views. While generally not mountainous, some routes include gentle elevation changes, offering a dynamic riding experience.
Yes, Winnebago County is well-suited for beginners and those seeking easier rides. Many routes are classified as easy, such as the Little Chute loop, which is just under 12 miles. These routes often provide smooth paths and minimal elevation gain, perfect for a relaxed outing.
Road cycling routes in Winnebago County often pass by beautiful natural features and local landmarks. You can enjoy views of Lake Winnebago, the Rock River, and various forest preserves. The The Friendship State Trail is a notable highlight, offering a pleasant cycling experience. Other points of interest include the Kimberly Point Lighthouse and the vibrant city of Oshkosh.
Absolutely. Many of the easy-rated routes are suitable for families. Paths like the Rock River Recreation Path and sections of the Grand Illinois Trail are paved and offer dedicated, safe spaces for cycling. These routes often pass through parks and scenic areas, making them enjoyable for all ages.
Parking is generally available at various access points for trails and parks throughout Winnebago County. For instance, Rock Cut State Park offers ample parking, and many trailheads, such as those for the Rock River Recreation Path, have designated parking lots. It's advisable to check specific route details for the most convenient parking options.
The spring and summer months are ideal for road cycling in Winnebago County, when the weather is pleasant and the natural landscapes are in full bloom. You'll experience abundant wildflowers and lush greenery, especially around the forest preserves and lakes. Autumn also offers beautiful foliage for scenic rides.
Yes, many road cycling routes in Winnebago County pass through or near local communities like Appleton, Kimberly, and Kaukauna, where you can find cafes, restaurants, and other amenities. Routes such as the Kaukauna loop or the Little Chute loop offer opportunities to stop for refreshments.
The road cycling routes in Winnebago County are highly regarded by the komoot community, boasting an impressive average rating of 4.8 stars from over 10 reviews. Cyclists frequently praise the varied terrain, scenic river views, and the well-maintained paths that make for an enjoyable riding experience.
For more experienced riders looking for longer distances, the Fox Cities Paper Trail is a popular choice, spanning over 50 miles. This route offers varied terrain and an extensive ride through the region, providing a good challenge for those seeking a longer adventure.
Yes, several routes allow you to experience the natural beauty of the region's state parks. For example, the Guyette's – High Cliff State Park loop from Darboy takes you through or near High Cliff State Park, offering scenic views and a chance to explore the park's unique features.


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