4.8
(13)
181
riders
31
rides
Touring cycling routes in Winona County are characterized by the unique Driftless Region landscape, featuring dramatic bluffs, steep valleys, and meandering waterways. The region's topography includes the majestic Mississippi River Valley, offering varied terrain and scenic vistas. Extensive trail networks and scenic routes provide diverse cycling experiences, from paved paths to routes with significant elevation changes. This area was untouched by glaciers, resulting in a rugged and varied landscape ideal for touring cyclists.
Last updated: June 29, 2026
14
riders
71.9km
05:11
780m
780m
Hard bike ride. Very good fitness required. Mostly paved surfaces. Suitable for all skill levels.
4.5
(2)
11
riders
8.73km
00:29
10m
10m
Easy bike ride. Great for any fitness level. Mostly paved surfaces. Suitable for all skill levels.

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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.
2
riders
34.9km
02:16
320m
320m
Moderate bike ride. Good fitness required. Mostly paved surfaces. Suitable for all skill levels.
10
riders
Moderate bike ride. Good fitness required. Mostly paved surfaces. Suitable for all skill levels.
3
riders
60.8km
03:40
430m
430m
Moderate bike ride. Good fitness required. Mostly paved surfaces. Suitable for all skill levels.
6
riders
33.8km
02:33
120m
120m
Moderate bike ride. Good fitness required. Mostly paved surfaces. Suitable for all skill levels.
5
riders
45.9km
02:47
90m
90m
Moderate bike ride. Good fitness required. Mostly paved surfaces. Suitable for all skill levels.
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La Crosse is fortunate to have Sister City relationships with eight cities around the world. These cities include Bantry, Ireland; Dubna, Russia; Epinal, France; Førde, Norway; Friedberg, Germany; Luoyang, China; Kumbo, The Republic of Cameroon, West Africa; and Junglinster, Luxembourg. Each of these relationships is unique and features cooperative efforts in such diverse activities as health care, education, sports, the arts, government agencies and public policy, business, and many others La Crosse's business activity along with the varied cultural backgrounds of the citizens has resulted in an environment that makes foreign visitors welcome and is supportive of a variety of cultural activities and events. Many of these events are supported and coordinated by the City’s International Committee. The International Committee has representation from each of our Sister Cities and from citizens interested in promoting international awareness and citizen diplomacy.
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Lots of nature, but be sure to stay on the paths
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This is the promenade on the Mississippi
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Many of the marsh trails are paved or hard-packed dirt, making it a great place for riding. This is good place to look for waterfowl and other wetland fauna, and there is a fishing pier and picnic area nearby.
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This scenic route winds along the bluffs above the Mississippi River, with views across the water and the rolling green farmland.
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The park goes right up to the water's edge, and there are plenty of nice grassy areas to hand out by the river in the shade. There are some paved trails, and sometimes the park will hold events at the band shell or for Riverfest.
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This bridge crosses the east channel of the Mississippi River connecting downtown La Crosse to Barron Island. The bridge is actually two bridges, the Cass Street Structure and the Cameron Avenue Structure, together they form The Mississippi River Bridge.
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Winona County offers a diverse selection of over 30 touring cycling routes. These routes cater to various skill levels, with 17 easy and 15 moderate options, ensuring there's a suitable ride for almost everyone.
The terrain in Winona County is characterized by the dramatic Mississippi River Valley, featuring majestic bluffs, lush valleys, and quiet streams. You'll find both paved paths, such as those around Lake Winona, and segments of the Mississippi River Trail. Some routes, like the La Crosse Marsh – Riverside Park loop from La Crosse, include more significant elevation changes, offering varied challenges and scenic views.
Yes, Winona County has several family-friendly options, particularly the routes around Lake Winona. The Lake Winona Park loop from Winona is an easy, paved 5.4-mile (8.7 km) trail that is perfect for a leisurely ride with the family. Lake Winona offers over 5 miles of paved paths, ideal for all ages.
Winona County's routes offer breathtaking views of the Mississippi River Valley and its iconic bluffs. You can encounter natural features like Sugar Loaf and King's Bluff Overlook. The region is also a significant spot for birdwatching, located in the heart of the Mississippi Valley Flyway, attracting over 280 species of birds throughout the year.
Yes, many of the touring cycling routes in Winona County are loops, providing convenient starting and ending points. Examples include the popular Lake Winona Park loop from Sugar Loaf and the more challenging La Crosse Trailhead – West Salem Bike Depot Park loop from La Crosse.
Winona County offers year-round cycling opportunities. The bluffs showcase magnificent colors throughout the seasons, from vibrant greens in summer to snowy branches in winter. Spring and fall provide comfortable temperatures and stunning scenery, while winter offers unique fat biking experiences. The annual tundra swan migration in the fall is also a highlight for nature enthusiasts.
Many routes, especially those around Lake Winona and within state parks like Great River Bluffs and John A. Latsch, offer designated parking areas. For specific parking information related to various trails and parks, you can consult the Winona County Parks & Trails website: winonacounty.gov.
The area is highly rated by the komoot community, with an average score of 5.0 stars from 8 reviews. Touring cyclists often praise the diverse landscapes, the scenic views of the Mississippi River Valley, and the well-maintained paths, especially around Lake Winona. The variety of easy and moderate routes also makes it appealing to a broad range of cyclists.
Yes, Winona County is part of the larger Mississippi River Trail (MRT), which offers extensive long-distance cycling. Within the komoot selection, routes like the Bike loop from La Crosse, at over 27 miles (44 km), provide a good option for longer rides, traversing varied landscapes along the river.
While specific public transport access directly to trailheads can vary, Winona city itself has public transportation options. For routes starting further afield, such as the Bike loop from Trempealeau National Wildlife Refuge, personal vehicle transport to the starting point is generally recommended.
While most routes in Winona County are classified as easy or moderate, some moderate routes offer more significant elevation gains and longer distances, providing a good challenge. For instance, the La Crosse Trailhead – Riverside Park loop from La Crosse features over 1000 feet (325 meters) of elevation gain over its 22.7 miles (36.6 km), making it a more demanding ride.
Yes, Winona County hosts cycling events. A premier event is the "Ride the Ridges" bicycle tour, which features challenging routes ranging from 23 miles to a century. This event showcases the amazing scenery of the Mississippi and its valley, majestic bluffs, and quiet streams. You can find more information about this event on the Visit Winona website: visitwinona.com.


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