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Road cycling around Oshkosh offers diverse routes across varied landscapes, centered around prominent waterways. The region is characterized by the expansive Lake Winnebago and the Fox River, providing scenic paths along their shores. Cyclists can explore a mix of woodlands, open fields, prairies, wetlands, and farmland, with many routes featuring flat terrain. While many trails are accessible, some routes offer moderate options for those seeking more challenging rides.
Last updated: July 2, 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.
4
riders
13.4km
01:01
20m
20m
Moderate road ride. Great for any fitness level. Some segments of this route may be unpaved and difficult to ride.

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1
riders
Easy road ride. Great for any fitness level. Mostly well-paved surfaces and easy to ride.
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Popular around Oshkosh
Big Lake Butte des Morts is freshwater and is part of the Winnebago Pool of lakes. Water enters via the Fox River and Wolf River. French settlers named it "Butte des Morts" after a close-by Native American burial mound.
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The Wiouwash State Trail is a rail trail that is maintained by the efforts of four counties. It is also named after these four counties: Winnebago, Outagamie, Waupaca, and Shawano counties.
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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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Doty Cabin is the historic replica of James Duane Doty's house. The original was built from 1844 to 1845. The cabin is only open to go inside from June through Labor Day, from 12:00 p.m. to 4:00 p.m. Admission is free, but donations are appreciated.
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This light was built in 1945, thanks to the work of local activist Helen Kimberly Stuart. It sits on the shore where Lake Winnebago flows into the Lower Fox River. The lighthouse has been listed on the National Register of Historic Places since 2013.
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Lake Winnebago is Wisconsin's largest lake that is entirely within the state. It was formed around 12,000 years ago from glacial activity and ice. It's a great place to enjoy the outdoors. You can windsurf, boat, fish and hike around the lakeshore. In winter, you can ice fish and skate too.
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Komoot features a selection of road cycling routes around Oshkosh, offering diverse experiences for cyclists. Currently, there are 3 routes detailed in this guide, with many more available on komoot for you to explore.
Yes, Oshkosh offers routes suitable for various skill levels. For an easier ride, consider the Lake Winnebago – The Friendship State Trail loop from 1516 So. Commercial, which is rated as easy and covers 16.1 miles (25.9 km) along Lake Winnebago shores and the Friendship State Trail. The region's generally flat terrain, especially on trails like the Wiouwash State Trail, also makes many paths accessible for families.
Road cycling routes in Oshkosh often feature picturesque views of Lake Winnebago and Lake Butte des Morts. You can also enjoy the natural beauty of woodlands, open fields, prairies, and wetlands. The Lake Butte des Morts loop from Oshkosh offers direct views of the lake and surrounding natural features. The Oshkosh Riverwalk provides scenic paved paths along the Fox River downtown, offering views of natural riverbanks and historic architecture.
For those seeking longer rides, the Fox Cities Paper Trail is a substantial option, spanning 50.3 miles (80.9 km) and traversing varied scenery including woodlands and open fields. Additionally, the region offers routes like the 101-mile 'Oshkosh Century' route around Lake Winnebago for experienced cyclists looking for a significant challenge.
Yes, the Wiouwash State Trail, a significant draw for cyclists, is dog-friendly. Dogs are welcome on this trail, provided they are kept on a leash.
The best time for road cycling in Oshkosh is typically during the spring, summer, and fall months when the weather is mild and pleasant. These seasons offer ideal conditions to enjoy the diverse landscapes, from blooming prairies to vibrant autumn foliage. Winter cycling is possible but requires appropriate gear for colder temperatures and potential snow or ice.
Yes, many routes in Oshkosh are designed as loops, allowing you to start and end at the same point. The Lake Butte des Morts loop from Oshkosh is a popular moderate circular route. Another option is the Lake Winnebago – The Friendship State Trail loop from 1516 So. Commercial, which offers a scenic loop experience.
Many popular trails and parks in Oshkosh offer designated parking areas. For instance, Menominee Park, located on the shores of Lake Winnebago, provides parking and access to scenic trails. Specific trailheads for routes like the Wiouwash State Trail also typically have parking facilities. It's advisable to check local park and trail websites for detailed parking information.
Some state trails in Wisconsin, including parts of the Wiouwash State Trail, may require a state trail pass for cyclists aged 16 and older. These passes can often be purchased at self-registration stations along the trails or online through the Wisconsin DNR website. It's always a good idea to check the specific requirements for the trail you plan to ride.
Yes, Oshkosh has several areas where you can find amenities like cafes and pubs. The Oshkosh Riverwalk, which runs through downtown, offers access to various restaurants and shops. Routes that pass through or near urban centers will generally have more options for refreshments and dining. Menominee Park also has facilities and is close to city amenities.
The terrain around Oshkosh is quite varied. Many routes, especially rail-trails like the Wiouwash State Trail, are flat and feature crushed-limestone or paved surfaces. Other routes, particularly those around Lake Winnebago and Lake Butte des Morts, offer a mix of paved roads and some moderate elevation gains. You'll cycle through woodlands, open fields, tallgrass prairies, wetlands, and farmland.
While many routes are relatively flat, some options provide more challenge. The 101-mile 'Oshkosh Century' route around Lake Winnebago is a significant long-distance ride. Additionally, the 'Rails-to-Gravel' route on the north side of Winnebago County combines gravel trails with lower-traffic roads and paved sections, offering a diverse and potentially more challenging experience for those looking to explore different terrains.


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