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Routes
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Winona County

Routes
Hikes

Winona County

The best family-friendly hikes and walks in Winona County

4.8

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454

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37

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Family friendly hiking trails in Winona County are characterized by dramatic river valley bluffs, lush hardwood forests, and views of the Mississippi River. The region's topography features iconic bluffs, including Sugar Loaf, and the expansive Mississippi River with its backwaters. These natural features provide a diverse landscape for outdoor activities, with trails winding through forests and along waterways.

Best family friendly hiking trails in Winona County

  • The most popular family friendly hiking route is Riverside Park Loop, a 1.1 miles (1.8 km) trail that takes 28 minutes to complete. This easy path offers views along the river.
  • Another top favourite among local hikers is Apple Blossom Overlook Trail, an easy 0.7 miles (1.2 km) path. This route features a gentle ascent to an overlook with scenic views.
  • Local hikers also love the Mississippi River Trail, a 1.4 miles (2.3 km) trail leading through riverfront parkland, often completed in about 36 minutes.
  • Hiking in Winona County is defined by river valley bluffs, hardwood forests, and the Mississippi River. The network offers 36 routes, with 19 easy options suitable for various ability levels.
  • The routes in Winona County are highly rated by the komoot community with an average score of 4.8 stars from over 20 reviews. More than 400 hikers have used komoot to explore Winona County's varied terrain.

Last updated: May 10, 2026

5.0

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#1.

Whitewater Chimney Rock Loop

1.00km

00:22

30m

30m

Hike the moderate 0.6-mile Whitewater Chimney Rock Loop in Whitewater State Park, featuring stairs, river views, and the iconic Chimney Rock

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Moderate

Hike the easy 4.8-mile Root River State Trail from Rushford to Peterson, enjoying scenic bluffs, the Root River, and charming small towns.

Easy
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1.83km

00:28

0m

10m

Enjoy an easy 1.1-mile hike on the Riverside Park Loop, featuring river views and the International Friendship Garden in La Crosse.

Easy

The Apple Blossom Overlook Trail is an easy 0.8-mile hike in La Crescent, offering panoramic views of the Mississippi River Valley.

Easy

3

hikers

Hike the easy 1.5-mile Mississippi River Trail in La Crosse's Riverside Park, offering scenic views of the Mississippi River and its iconic

Easy
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Popular around Winona County

Family-friendly hikes in Richard J. Dorer Memorial Hardwood State Forest

Tips from the Community

tcbscott
October 5, 2025, Swimming Beach

Today was the first time I have been to park and seen people in the water, but it was in the 90's in October. I mostly come here in the late fall

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Great bridge, part of my memories of hiking here every year.

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Peterson town theme is Gnomes, not sure why, but they have an awesome giant gnome next to their sign, right on the bike path!

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tcbscott
September 28, 2025, Barn and Pump House

Founder of Peterson's barn and the pump house

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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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This is one of the best views of the Rushford sign on the bluff I found from the bike trail.

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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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Wolfgang-WS711
September 1, 2025, Riverside Park

This is the promenade on the Mississippi

Translated by Google

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Frequently Asked Questions

How many family-friendly hiking trails are available in Winona County?

Winona County offers a fantastic selection of family-friendly hiking trails. You'll find over 30 routes specifically curated for families, ranging from easy strolls to more moderate adventures. These trails provide diverse experiences across the region's beautiful bluffs, forests, and riverbanks.

What kind of terrain can we expect on family hikes in Winona County?

The terrain in Winona County is quite varied, offering something for every family. Many trails feature gentle, paved paths, especially around Lake Winona and along the Mississippi River. Other routes, particularly those ascending the bluffs, can include short, steep climbs and winding paths through hardwood forests, providing more of a challenge and rewarding views. For example, the Whitewater Chimney Rock Loop offers a moderate experience with some elevation.

Are there any easy, short hikes suitable for families with young children?

Absolutely! Winona County has several easy and relatively short trails perfect for families with young children. The Riverside Park Loop is a great option, offering a flat, accessible walk. Another excellent choice is the Mississippi River Trail, which provides a leisurely experience along the river with minimal elevation gain.

What are some notable landmarks or viewpoints we can see on these trails?

Winona County is famous for its stunning bluffs and river views. Many family-friendly trails lead to or pass by incredible viewpoints. Don't miss the iconic Sugar Loaf, offering panoramic views of the city and the Mississippi River. Other highlights include Coyote Point Overlook and King's Bluff Overlook, both providing breathtaking vistas of the river valley. The Chimney Rock Footbridge is also a unique feature to explore.

Are there any circular routes that are good for families?

Yes, several family-friendly trails in Winona County are circular, making for convenient outings. The Riverside Park Loop is a great example, offering a pleasant, easy circuit. For a slightly more adventurous loop, consider the Whitewater Chimney Rock Loop, which provides a moderate challenge and scenic beauty.

Can we bring our dog on the family-friendly trails?

Many trails in Winona County are dog-friendly, but it's always best to check specific park regulations before you go. Generally, dogs are welcome on leash in most state parks and on many city trails. Always remember to clean up after your pet to keep the trails enjoyable for everyone.

What is the best time of year to go hiking with family in Winona County?

Winona County offers beautiful hiking experiences throughout the year. Spring brings lush greenery and blooming wildflowers, while summer provides warm weather perfect for outdoor adventures. Autumn is particularly spectacular, with the hardwood forests transforming into vibrant displays of fall foliage. Even winter offers unique opportunities for snow-dusted walks, though some trails may be less accessible. Each season has its own charm!

Are there options for public transport or parking near the trailheads?

While public transport options directly to all trailheads might be limited, many popular family-friendly trails, especially those within the city of Winona or state parks, offer designated parking areas. For specific parking information, it's advisable to check the details for individual routes or consult local resources like Winona County Parks & Trails.

What do other hikers enjoy most about family-friendly trails in Winona County?

The family-friendly trails in Winona County are highly rated by the komoot community, with an average score of 4.8 stars. Reviewers often praise the stunning panoramic views from the bluffs, the well-maintained paths, and the diverse natural beauty, from the Mississippi River to the serene forests. Many highlight the accessibility and variety of trails that cater to different ages and abilities, making it a perfect destination for a family outing.

Are there any trails suitable for strollers or wheelchairs?

For families with strollers or those needing wheelchair accessibility, the paved paths around Lake Winona and sections of the Mississippi River Trail are excellent choices. These routes offer flat, smooth surfaces, ensuring a comfortable and enjoyable experience for everyone. The Riverside Park Loop is another easy, accessible option.

What should we bring for a family hike in Winona County?

For a comfortable family hike, consider bringing plenty of water, snacks, sun protection (hats, sunscreen), and insect repellent, especially during warmer months. Comfortable walking shoes are a must. Depending on the trail, a small first-aid kit, binoculars for birdwatching, and a camera to capture the scenic views are also great additions. Always check the weather forecast before heading out!

Most popular routes in Winona County

Hiking in Winona County

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Richard J. Dorer Memorial Hardwood State Forest

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