5.0
(8)
248
riders
47
rides
Road cycling routes in Winona County traverse a diverse landscape characterized by the Upper Mississippi River Valley. The region features dramatic bluffs, lush valleys, and tranquil streams, providing varied terrain for cyclists. Key natural features include the towering bluffs overlooking the Mississippi River, Lake Winona, and extensive forests. This area offers a mix of flat, paved paths and challenging routes with elevation changes.
Last updated: May 16, 2026
20
riders
60.7km
02:39
430m
430m
Moderate road ride. Good fitness required. Mostly well-paved surfaces and easy to ride.
10
riders
43.9km
01:55
290m
290m
Easy road ride. Great for any fitness level. Mostly well-paved surfaces and easy to ride.

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8
riders
36.3km
01:38
280m
280m
Easy road ride. Great for any fitness level. Mostly well-paved surfaces and easy to ride.
8
riders
44.5km
02:31
370m
370m
Moderate road ride. Good fitness required. Some segments of this route may be unpaved and difficult to ride.
5.0
(2)
9
riders
17.7km
00:53
60m
60m
Easy road ride. Great for any fitness level. Mostly well-paved surfaces and easy to ride.
5
riders
91.5km
03:50
470m
470m
Moderate road ride. Good fitness required. Mostly well-paved surfaces and easy to ride.
7
riders
75.9km
03:38
580m
580m
Moderate road ride. Good fitness required. Mostly well-paved surfaces and easy to ride.
8
riders
13.1km
00:36
50m
50m
Easy road ride. Great for any fitness level. Mostly well-paved surfaces and easy to ride.
7
riders
58.0km
02:25
370m
370m
Moderate road ride. Good fitness required. Mostly well-paved surfaces and easy to ride.
4
riders
24.3km
01:05
230m
230m
Easy road ride. Great for any fitness level. Mostly well-paved surfaces and easy to ride.
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Popular around Winona County
Impressive view from the bridge over the Mississippi, despite Labor Day - holiday - few boats on the Mississippi
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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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The widely visible landmark of the city of LaCrosse. LaCrosse is twinned with Friedberg (Bavaria).
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The Mississippi is the second-longest river in America (after the Missouri), and runs for around 2,340 miles all the way across the country through New Orleans. The road on bridge has a decent shoulder, and there is also a divided walkway where you can bike separate from traffic.
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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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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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Winona County offers over 45 road cycling routes, catering to various skill levels. You'll find a mix of easy lakeside paths and more challenging routes with significant elevation changes, all set against the backdrop of the Upper Mississippi River Valley.
The terrain in Winona County is diverse, characterized by the Upper Mississippi River Valley. Cyclists can expect dramatic bluffs, lush valleys, and tranquil streams. Routes range from flat, paved paths around Lake Winona to more challenging climbs with significant elevation changes in areas like the bluffs overlooking the Mississippi River.
Yes, Winona County has several easy routes suitable for families. The Lake Winona loop from Fairway Woods is a great option, offering a flat, paved path around Lake Winona with excellent views. Another accessible choice is the Roadbike loop from La Crescent, which is also rated as easy.
Winona County is considered a 'cyclist's paradise year-round.' While summer offers pleasant rides along riverfront paths, spring and fall are particularly popular for tackling bluff trails due to cooler temperatures and vibrant foliage. Even winter can offer unique fat biking adventures, though road cycling conditions may vary.
Many of the road cycling routes in Winona County are designed as loops, allowing you to start and end in the same location. Examples include the Riverside Park loop from La Crosse, which offers views of the Mississippi River, and the Lake Winona loop from Winona.
Winona County's routes offer breathtaking views of the Mississippi River Valley and its iconic bluffs. You can enjoy panoramic vistas from points like Coyote Point Overlook and King's Bluff Overlook. The prominent Sugar Loaf landmark also provides expansive views of the valley and river.
Yes, Winona County offers moderate routes with significant elevation changes for more experienced cyclists. The Mary of the Angels Chapel loop from La Crosse is a moderate route that includes climbs, providing a good challenge. Other routes traversing the bluffs also offer more demanding ascents.
The road cycling routes in Winona County are highly rated by the komoot community, with an average score of 5.0 stars. Cyclists often praise the stunning views of the Mississippi River and bluffs, the diverse terrain, and the variety of routes available for different skill levels, from easy lakeside paths to challenging climbs.
Yes, the Riverside Park – Tschumper Hill Views loop from La Crosse is an easy route that specifically highlights scenic views, including those from Tschumper Hill. Another option is the Tschumper Hill Views loop from La Crescent.
For general information on parks and trails within Winona County, you can visit the official county website. They often provide details on local amenities and regulations. You can find more information at winonacounty.gov.
Winona County is part of the larger Mississippi River Trail (MRT), which offers scenic segments along the river. Additionally, the Flyway Trail - Winona Connector links Winona to Buffalo County, WI, traversing bridges with stunning river views, providing options for longer rides beyond the immediate county.
Beyond the Mississippi River and its bluffs, you'll encounter diverse natural features. These include the tranquil Lake Winona, rugged limestone bluffs and pristine trout streams in Whitewater State Park, and the bluff lands, prairies, and forests of Frontenac State Park, which is home to over 260 bird species.


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