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Routes
Running Trails
United States
Minnesota

Winona County

The best running trails in Winona County

261

runners

42

runs

Jogging in Winona County offers diverse terrain within Minnesota's Driftless Region, characterized by dramatic bluffs, steep valleys, and the winding Mississippi River. The landscape features limestone bluffs, such as Sugar Loaf and Garvin Heights, providing elevated views. Runners can explore flood plain forests, prairie, and routes along the Mississippi River and Lake Winona. This varied topography creates a range of running experiences, from flat lakeside paths to more challenging trails with significant elevation changes.

Best jogging routes in Winona County

Last updated: May 12, 2026

22

runners

#1.

Lake Winona loop from Winona

8.61km

00:53

10m

10m

Moderate run. Good fitness required. Mostly paved surfaces. Suitable for all skill levels.

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Moderate

15

runners

Moderate run. Good fitness required. Mostly paved surfaces. Suitable for all skill levels.

Moderate
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Hard run. Very good fitness required. Sure-footedness, sturdy shoes and alpine experience required.

Hard

Moderate run. Good fitness required. Mostly paved surfaces. Suitable for all skill levels.

Moderate

6

runners

Easy run. Great for any fitness level. Mostly paved surfaces. Suitable for all skill levels.

Easy

7

runners

Moderate run. Good fitness required. Mostly paved surfaces. Suitable for all skill levels.

Moderate
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Popular around Winona County

Running Trails around Dresbach

Running Trails around Homer

Hiking in Winona County

Road Cycling Routes in Winona County

Cycling in Winona County

MTB Trails in Winona County

Tips from the Community

tcbscott
October 5, 2025, Chimney Rock Footbridge

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

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I love this big climb up the stairs and then into ladders. Would much rather climb it then descend it, so I usually park by the Nature Store, then you just hut across the road and up you go.

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Lots of nature, but be sure to stay on the paths

Translated by Google

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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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Zachary
June 27, 2025, La Crosse Marsh

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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Zachary
June 26, 2025, Riverside Park

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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Chimney Rock Footbridge is a historical bridge designed by N. Averill and built in 1935 by the Civilian Conservation Corps. It crosses Middle Fork Whitewater River.

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Inspiration Point is one of multiple peaks along State Highway 74 that are connected with nice hiking trails through the woods. With an elevation of about 1,036 feet, it offers nice views of the surrounding area.

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Frequently Asked Questions

How many running routes can I find in Winona County?

Winona County offers a diverse selection of over 35 running routes. These trails cater to various preferences, from easy, flat paths to more challenging routes with significant elevation changes, all set against the backdrop of the region's unique bluffs and river valleys.

Are there any easy or beginner-friendly jogging routes in Winona County?

Yes, Winona County has several easy running routes perfect for beginners or those seeking a relaxed jog. A popular choice is the Running loop from Winona, which is just under 4 kilometers with minimal elevation. The Lake Park Path, circling Lake Winona, also offers a flat, paved surface ideal for an easy run with scenic views.

What kind of terrain can I expect on running trails in Winona County?

The terrain in Winona County is quite varied due to its location in the Driftless Region. You'll find flat, paved paths along the Mississippi River and Lake Winona, as well as more challenging trails through limestone bluffs and steep valleys. Expect a mix of flood plain forests, prairie, and trails with significant elevation changes, offering diverse running experiences.

Are there any circular jogging routes in Winona County?

Yes, many of the running routes in Winona County are circular, allowing you to start and end at the same point. A prominent example is the Lake Winona loop from Winona, a 9-kilometer path that circles the lake, offering continuous scenic views. Another option is the Lake Winona loop from Homer, which is a longer, moderate 12.9-kilometer circular route.

What are some notable landmarks or scenic viewpoints along the running routes?

Winona County's running routes often feature stunning natural landmarks. You can enjoy breathtaking panoramic views from iconic bluffs like Sugar Loaf and Coyote Point Overlook. The Chimney Rock Footbridge – Coyote Point Overlook loop specifically highlights these features, offering dramatic vistas of the bluffs and river valleys.

Are there any family-friendly running trails in the area?

For families, the flatter, paved paths are generally the most suitable. The Lake Park Path around Lake Winona is an excellent choice, providing a safe and accessible environment for all ages with beautiful lake and bluff views. Sections of the Flyway Trail and Mississippi River Trail are also paved and offer easy running for families.

Can I bring my dog on the running trails in Winona County?

Many trails in Winona County are dog-friendly, but it's always best to check specific park or trail regulations before heading out. Generally, dogs are welcome on a leash in most public outdoor spaces. The Lake Park Path and many multi-use trails in Bluffside Park are popular choices for running with canine companions.

What is the best time of year for jogging in Winona County?

Spring, summer, and fall generally offer the most pleasant conditions for jogging in Winona County. Spring brings blooming wildflowers, summer provides lush greenery, and fall showcases vibrant foliage, especially along the bluffs. While winter running is possible, be prepared for snow and ice, particularly on unpaved trails. Always check local weather and trail conditions.

Are there any long-distance running options in Winona County?

Yes, for those looking for longer runs, the Mississippi River Trail (MRT) offers extensive paved sections that can be utilized for significant distances. While some parts use road shoulders, dedicated scenic segments are excellent for long-distance jogging. Additionally, combining loops or exploring the broader trail systems in parks like Bluffside Park can create longer routes.

Where can I find parking near the running trailheads?

Parking is generally available at popular trailheads and parks throughout Winona County. For routes around Lake Winona, you'll find parking facilities in Lake Park. For trails accessing the bluffs or river, look for designated parking areas at parks like Bluffside Park or along the Mississippi River. It's advisable to check specific route details on komoot for precise parking information.

What do other runners enjoy most about jogging in Winona County?

Runners frequently praise Winona County for its stunning natural beauty and diverse landscapes. The dramatic bluffs, the serene Mississippi River, and Lake Winona provide inspiring backdrops. Many appreciate the variety of trails, from flat, accessible paths to challenging climbs, and the opportunity to experience unique ecosystems like flood plain forests and prairie.

Are there any running routes that offer shade?

Yes, many running routes in Winona County pass through forested areas, providing welcome shade, especially during warmer months. Trails within Bluffside Park and Great River Bluffs State Park often wind through wooded sections. The Chimney Rock Footbridge – Coyote Point Overlook loop, for instance, leads through bluffs and river valleys that include shaded segments.

Most popular routes in Winona County

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