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Urban hiking trails in Winona County offer accessible paths primarily along the Mississippi River and within city parks. The region is characterized by its location in the Driftless Area, featuring bluffs and river valleys, though the urban routes tend to be flatter. These trails provide opportunities to explore the city's natural surroundings and riverfront areas. The landscape includes riverine environments and green spaces suitable for easy walks.
Last updated: July 7, 2026
1.83km
00:28
0m
10m
Easy hike. Great for any fitness level. Easily-accessible paths. Suitable for all skill levels.
3
hikers
2.35km
00:36
10m
10m
Easy hike. Great for any fitness level. Easily-accessible paths. Suitable for all skill levels.

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6
hikers
Easy hike. Great for any fitness level. Easily-accessible paths. 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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This is the promenade on the Mississippi
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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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From the northwest corner of Riverside Park of La Crosse, you can see a triple confluence of rivers: to your left, the Mississippi River; straight ahead, the Black River; and on your right, the La Crosse River.
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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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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 selection of urban hiking trails, with three easy routes currently featured in this guide. These trails are generally flat and accessible, perfect for a leisurely walk through the city's natural surroundings.
Urban hikes in Winona County, particularly those along the riverfront, feature mostly flat and paved or well-maintained paths. While the broader region is known for its dramatic bluffs, the urban trails tend to offer gentler gradients, often winding through parks and along the Mississippi River. For example, the Riverside Park Loop is largely flat, providing an easy walking experience.
Yes, even on urban trails, you can find scenic spots. The Mississippi River itself provides constant picturesque views. While the urban routes in this guide are generally flat, the city of Winona is surrounded by impressive bluffs. You can find stunning panoramic views from nearby highlights like Sugar Loaf or Coyote Point Overlook, which are easily accessible from the city.
Absolutely. The urban trails in Winona County are generally easy and well-suited for families. Routes like the Mississippi River Trail are flat and relatively short, making them ideal for walks with children. The paved surfaces also make them accessible for strollers.
Most urban parks and trails in Winona County are dog-friendly, provided your pet is kept on a leash. It's always a good idea to check specific park regulations before you go, but generally, you can enjoy a walk with your canine companion on routes such as the Riverside Park Loop.
Spring, summer, and fall are excellent seasons for urban hiking in Winona County. Spring brings blooming flora, while summer offers lush greenery and warm weather. Autumn is particularly beautiful with the vibrant fall foliage on the surrounding bluffs. Even in winter, cleared paths can offer crisp, scenic walks, especially along the river, though conditions may vary.
Yes, many urban trails in Winona County are designed to showcase the majestic Mississippi River. The Mississippi River Trail and the Riverside Park Loop both offer continuous views of the river, its islands, and the dramatic bluffs on the opposite bank.
The komoot community rates the hiking experience in Winona County highly, with an average score of 4.8 stars from 20 reviews. Hikers often praise the accessibility of the trails, the beautiful river views, and the opportunity to experience nature within a city setting. The flat, well-maintained paths are frequently highlighted as a positive aspect for easy, enjoyable walks.
Yes, several urban routes in Winona County are circular, offering convenient starting and ending points. The Riverside Park Loop is a great example, allowing you to complete a full circuit without retracing your steps. Another option is the A Triple Confluence of Rivers – Riverside Park loop from La Crosse, which also forms a loop.
Parking is generally available near popular urban trailheads and parks in Winona County. For trails like those around Riverside Park, you'll typically find designated parking areas. As these are urban routes, many are easily accessible from city streets and public parking lots.
Winona County is located in the Mississippi Valley Flyway, making it an excellent spot for birdwatching, even on urban trails. The riverfront paths, such as the Mississippi River Trail, provide opportunities to spot eagles, hawks, and various migratory birds, especially during spring and fall migrations.


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