4.5
(4)
59
riders
8
rides
Touring cycling around Winona is characterized by its location within the Mississippi River Valley and the unique Driftless Region. The landscape features dramatic bluffs, steep valleys, and the winding Mississippi River, providing varied terrain for cyclists. Lake Winona, situated within the city, offers flat, paved paths, while the surrounding bluffs provide elevated experiences. This geological area, untouched by glaciers, presents a distinctive topography of streams and valleys.
Last updated: May 17, 2026
4.5
(2)
10
riders
9.02km
00:31
20m
20m
Easy bike ride. Great for any fitness level. Mostly paved surfaces. Suitable for all skill levels.
5
riders
13.9km
00:52
70m
70m
Easy bike ride. Great for any fitness level. Mostly paved surfaces. Suitable for all skill levels.

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2
riders
36.6km
02:14
290m
290m
Moderate bike ride. Good fitness required. Mostly paved surfaces. Suitable for all skill levels.
2
riders
57.4km
03:24
360m
360m
Moderate bike ride. Good fitness required. Mostly paved surfaces. Suitable for all skill levels.
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Popular around Winona
Lake Winona Park features many picnic tables, shelters, a disc golf course, and a bike trail that goes entirely around the lake.
2
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This shop is a combination bike shop, coffee shop and ice cream shop. You can get your bicycle repaired while sipping an expresso or licking an ice cream cone. The ice cream is sold in a restored train caboose right next door. Sandwhiches are also served. While you visit you can pick up good information on biking opportunities in Trempealeau County. You can also buy a trail pass to the Great River State Trail.
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The Trempealeau Hotel is an iconic destinatioon in Trempealeau. Right on the waterfront with great views of the barge and train traffic as well as the flights of migrating birds overhead. Great food. Live entertainment.
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On a hot day this park offers shade and a place to sit for a picnic.
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Winona offers a selection of 8 touring cycling routes, catering to various preferences. These routes are highly rated by the komoot community, with an average score of 5.0 stars.
The touring cycling routes around Winona primarily feature easy to moderate difficulty levels. You'll find 5 easy routes, perfect for a relaxed ride, and 3 moderate routes for those seeking a bit more challenge. There are no difficult routes listed in this guide.
Yes, Winona has several family-friendly options, particularly the easy routes. The Lake Winona Park loop from Sugar Loaf is an excellent choice, offering flat, paved paths with scenic views of Lake Winona and the surrounding bluffs, ideal for all ages.
Many of the touring cycling routes in Winona are designed as loops, allowing you to start and end at the same point. Examples include the Lake Winona Park loop from Sugar Loaf, the Trempealeau Hotel loop from Perrot State Park, and the Bike loop from Trempealeau National Wildlife Refuge.
Winona's touring cycling routes offer diverse and stunning scenery, characterized by the majestic Mississippi River Valley and the unique Driftless Region. You'll encounter dramatic bluffs, winding waterways, and lush valleys. Routes often provide panoramic views of the river, especially from elevated points, and pass through natural areas like the Upper Mississippi River National Wildlife and Fish Refuge.
Yes, several routes offer views of or access to notable landmarks. You can enjoy views of Sugar Loaf bluff, a prominent feature of the Winona skyline. Other routes may provide glimpses of Trempealeau Bay and Trempealeau Mountain. For cultural stops, the Minnesota Marine Art Museum is also an attraction in the area.
The best time for touring cycling in Winona is typically from spring through fall. During these seasons, the weather is generally pleasant, and the natural beauty of the Mississippi River Valley and bluffs is at its peak. Spring brings fresh greenery, summer offers warm rides, and fall showcases vibrant foliage.
For those looking for longer rides, the Lake Winona Park loop from Winona is a moderate 36.6 km (22.7 miles) route with significant elevation gain. Another option is the Stockyards – Dodge Public Park loop from Goodview, which is a moderate 57.4 km (35.7 miles) route, offering a more extensive touring experience.
While specific parking details for each trailhead are best checked locally, Winona is generally well-equipped for outdoor recreation. For broader information on outdoor recreation facilities, including potential parking areas, you can consult the city's official resources at winonamn.gov. Public transport options may be limited directly to trailheads, so planning for car access is often recommended.
The area is highly rated by the komoot community, with an average score of 5.0 stars. Reviewers often praise the diverse terrain, from flat lake loops to routes with bluff views, and the overall scenic beauty of the Mississippi River Valley and the unique Driftless Region.
Yes, nearby state parks like Great River Bluffs State Park and John A. Latsch State Park offer additional trails and stunning views of the Mississippi River from atop limestone bluffs. While primarily known for hiking, they contribute to the overall outdoor appeal and scenic backdrop for touring cyclists in the region.
Absolutely. Winona offers several paved trails, making for smooth touring cycling experiences. The Lake Winona Park loop is a prime example of a paved path. Additionally, the city has other paved options like the 40th Street Bike Path and 48th Street Bike Path, providing accessible routes for cyclists.


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