4.8
(11)
186
riders
32
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: May 17, 2026
5.0
(1)
13
riders
8.73km
00:29
10m
10m
Easy bike ride. Great for any fitness level. Mostly paved surfaces. Suitable for all skill levels.
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.

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5
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.
5
riders
60.8km
03:40
430m
430m
Moderate bike ride. Good fitness required. Mostly paved surfaces. Suitable for all skill levels.
8
riders
43.9km
02:33
120m
120m
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.
7
riders
23.5km
01:22
70m
70m
Easy bike ride. Great for any fitness level. Mostly paved surfaces. Suitable for all skill levels.
5
riders
45.8km
02:47
90m
90m
Moderate bike ride. Good fitness required. Mostly paved surfaces. Suitable for all skill levels.
5
riders
19.3km
01:12
70m
70m
Easy bike ride. Great for any fitness level. Mostly paved surfaces. Suitable for all skill levels.
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Popular around Winona County
Looks like a neat little place, and it's right next to the bowling alley which has more food and drink options. Plus they have volleyball courts.
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I'm guessing at different times the picnic area had more amenities, right now it was one table. And the only thing eating back there was the mosquitos chomping on me when I stopped to take a picture.
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I saw a highlight Komoot created for Cushing Peak, so I wanted to get a picture of it today on my bike ride.
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There was a ton of tree debris pushed up against this big bridge, maybe the longest bridge on the trail between Rushford and Houston
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A bunch of crushed rock put between fencing to hold back the rock. Haven't seen one like this before.
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This is one of the best views of the Rushford sign on the bluff I found from the bike trail.
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A nice place to park and get on the trail. It was very busy today for late September, but since it was also in the upper 70's and sunny, no big surprise. Looks like they are restoring the depot. I thought when I was here 6 years ago the depot was open. I like the small collection of vintage buildings, and there are a few bar and grills near the parking lot for lunch/dinner.
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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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