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Best dog friendly hiking trails in Winona County, Minnesota, are found within the distinctive Driftless Region, characterized by rugged topography of dramatic bluffs, steep valleys, and winding waterways. This area features rich hardwood forests, particularly on the bluffs' slopes, and restored prairies. The majestic Mississippi River plays a central role, offering expansive views and diverse ecosystems.
Last updated: July 7, 2026
4
hikers
4.21km
01:07
40m
40m
The Snakeroot, Blazingstar and Quarry Loop Trail offers a delightful journey through the La Crosse Blufflands, showcasing varied scenery from scrub forest to dense woods. You'll traverse areas that hint…
5.0
(1)
11
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2.65km
00:43
40m
40m
The Compass Loop in Grandad Bluff Park offers a refreshing escape into nature, winding through scenic landscapes that lead to truly expansive views. You'll experience a modern flow trail, generally…

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8
hikers
3.20km
00:51
40m
40m
The Quarry Trail Loop in La Crosse, Wisconsin, offers an easy hiking experience, perfect for a quick outing. This 2.0-mile (3.2 km) route features a modest 115 feet (35 metres)…
6
hikers
Moderate hike. Good fitness required. Mostly accessible paths. Sure-footedness required.
6
hikers
Moderate hike. Great for any fitness level. Mostly accessible paths. Sure-footedness required.
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You can get great views over the forest here. Don't forget to ride a little farther west to Grandad Bluff, where the already-good views become even better.
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Looking out over the mighty Mississippi River valley stands the aptly named Tortoise Rock. From the perfect vantage point, this boulder bears an uncanny resemblance to a mighty ancient tortoise. Let your imagination wander as you take in the sweeping landscape.
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From this viewpoint 600 feet above La Crosse, you get great views of the Mississippi River, Wisconsin, Minnesota, as well as Iowa. Also, a wonderful spot to take in the vibrant fall colors.
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With its rolling hills and diverse terrain, Upper Hixon Forest offers mountain bikers a peaceful wilderness escape right in the city. Miles of paths wind through lush greenery and rocky outlook. Seek out this hidden gem when you crave woodland solitude and scenic vistas while enjoying an exhilarating, rugged ride over the ups and downs of this beautiful landscape.
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This road leads up to the Grandad Bluff View Point. Bikes are not allowed on the short trail out to the official overlook, so you will need to walk your bike. From the official viewpoint, you can see the Mississippi River, Wisconsin, Minnesota, as well as Iowa.
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Fantastic viewpoint over Hixon Forest and the surrounding areas.
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From this viewpoint 600 feet above La Crosse, you get great views of the Mississippi River, Wisconsin, Minnesota, as well as Iowa. Also a wonderful spot to take in the vibrant fall colors.
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500' climb to one of the best views of the Mississippi.
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There are currently 4 dog-friendly hiking trails listed in Winona County, offering a variety of experiences for you and your canine companion. Three of these are rated as easy, and one is moderate.
Yes, Winona County offers several easy dog-friendly loop trails. For a pleasant walk, consider the Compass Loop, which is just over 2.6 km. Another great option is the Quarry Trail Loop, spanning about 3.2 km, or the slightly longer Snakeroot, Blazingstar and Quarry Loop Trail at 4.2 km.
Winona County, part of the unique Driftless Region, offers stunning scenery characterized by dramatic bluffs, steep valleys, and winding waterways. You'll find trails winding through rich hardwood forests, past restored goat prairies, and offering expansive views of the Mississippi River Valley. Many trails provide breathtaking vistas from blufftops, showcasing the region's untouched geological wonders.
Absolutely! The region is known for its spectacular overlooks. While specific trails may not lead directly to every viewpoint, many hikes offer glimpses of the dramatic bluffs and the Mississippi River. Notable viewpoints in the area include Coyote Point Overlook and King's Bluff Overlook, which provide magnificent views of the river and surrounding landscape. The iconic Sugar Loaf also offers panoramic views of the city of Winona and the Mississippi River.
Winona County offers beautiful hiking experiences year-round. Spring brings lush greenery and blooming wildflowers, while summer provides warm weather for exploring. Fall is particularly stunning with vibrant autumn colors across the hardwood forests. Even winter can be magical, with trails like those in Bluffside Park suitable for hiking in all seasons, offering serene, snow-covered landscapes.
Yes, for a more challenging and longer dog-friendly hike, consider the Grandad Bluff Viewpoint loop from University of Wisconsin-La Crosse. This moderate trail covers approximately 5 km with a significant elevation gain, rewarding you with impressive views.
The komoot community highly rates the dog-friendly trails in Winona County, with an average score of 4.8 out of 5 stars from 20 ratings. Reviewers often praise the stunning bluff views, the diverse natural landscapes, and the well-maintained paths that make for enjoyable outings with their dogs.
Yes, Winona County is a fantastic destination for bird watching, especially as it lies within the Mississippi Valley Flyway. You and your dog can spot over 280 species of birds in the bluffs, valleys, and backwaters. The Prairie Island Nature Trail, though not explicitly listed as dog-friendly in this guide, is known for spotting eagles, deer, hawks, and migratory birds in its wooded lowlands, indicating the rich avian life in the area.
When hiking with your dog in Winona County, always ensure they are on a leash, especially in state parks and natural areas, to protect wildlife and other hikers. Be mindful of the rugged terrain, particularly on bluff trails, and carry enough water for both yourself and your dog. Always pack out what you pack in, including waste.
For more details on the natural beauty and attractions of the area, you can visit the official Winona County tourism website. They offer insights into the region's unique landscapes and photo opportunities. You can explore more at visitwinona.com.
Many trails in Winona County provide stunning views of the Mississippi River. The region's defining bluffs, carved by ancient meltwater, offer expansive vistas. Trails within areas like Great River Bluffs State Park and Bluffside Park are particularly known for their picturesque views of the Mississippi River Valley and its backwaters.


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