Looking for the best trails around Winona?

Explore the best rated trails in Winona, MN, whether you're looking for an easy walking trail or a bike trail like the Elroy-Sparta State Trail and John Wellner Memorial Trail . With more than 61 trails covering 339 miles you're bound to find a perfect trail for you. Click on any trail below to find trail descriptions, trail maps, photos, and reviews.

Recent Trail Reviews

Root River State Trail

Loved this trail

July, 2024 by pauldspain

Only did about 11 miles round trip from Houston. Very rural and scenic with river views, hills, fields and heavy tree overgrowth. I would love to do the entire journey. That is for next time!!!

La Crosse River State Trail

Buy pass first!

July, 2024 by rembrandreadoran

Don’t waste time looking for a physical location to buy pass prior to biking. Go online. And buy a daily pass in 2 minutes for $5.23. I lost 75 minutes driving to 3 locations before I realized online was an easy option.
https://dnr.wisconsin.gov/topic/parks/admission/trailpass

Flat trail with plenty of benches along the way to rest.

Root River State Trail

Great Ride

June, 2024 by dpoquette

I rode the section between Rushford and Whalen and it was a great ride. Lots of canopy on a very hot and humid day. You could see that the trail had been cleaned up. Unfortunately, just after we rode it, a flash flood warning was issued so, I don’t know if there was any damage. I would definitely ride it again. The previous two reviewers who rode it in June 2024 gave the trail a 1 & 2 stars just because the trail wasn’t cleaned up were too harsh. Give the volunteers and crew a chance to clean things up.

Accordion

Harmony-Preston Valley State Trail

Cleanup debris

June, 2024 by penfre73680

This trail has so many limbs and branches that I saw three people changing flat tires along this trail. Clean it up because riders don’t want to constantly be battling debris on trail.

Root River State Trail

clean up trail

June, 2024 by penfre73680

This trail needs significant attention to clean up all the debris on the pavement . Low branches and old pavement make this trail marginal at best. Use some of Minnesota tax money to cleanup or have locals that benefit from trail clean up all the debris

Root River State Trail

pick up the debris

June, 2024 by peenfre7368

Lots of debris from Lanesboro to Fountain. Don’t know if this is normal but the trail needs maintenance. Saw several people with flat tires from all the debris on trail.

Harmony-Preston Valley State Trail

Some trail work has been completed to improve the on and offs of the bridges.

June, 2024 by mankato

Some trail work has been completed to improve the on and offs of the bridges.

Harmony-Preston Valley State Trail

Great ride, less traffic and wonderful views and vistas.

June, 2024 by mankato

Great ride, less traffic and wonderful views and vistas.

Harmony-Preston Valley State Trail

trail needs maintenance

June, 2024 by peenfre7368

This trail is full of sticks and branches and needs more maintenance to be a pleasurable ride. Does the county or state maintain this trail?

Chippewa River State Trail

Segment from Durand trailhead to Red Cedar Trail

June, 2024 by djmmsherman

We rode this trail in late May 2024 and listened to the reviews, so I can only comment on the western part of this trail, from the Durand trailhead, riding about 6.5 miles to the intersection with the Red Cedar Trail and then we headed north on that trail. Other reviews say past the intersection, the trail needs work, so we followed that advice. The trail out of Durand is great -- paved and beautiful biking with tree canopy and the point where the trail intersects with the Red Cedar is clearly marked. The portion we did was great.

Root River State Trail

Always a favorite

June, 2024 by djmmsherman

We've been on this trail several times and it's consistently great. This time, we started at the trailhead in Lanesboro, biked west and up to Fountain, turned around for a nice mostly-downhill ride, stopped back in Lanesboro for lunch at Pedal Pushers, then onward east toward Rushford. Trail in great shape except for a felled tree from a storm the night before. But easy enough to pick up the bike and carry it over the tree. Aroma Pies in Whalen is a must-do; both coconut cream and banana cream are highly recommended! A nice treat for our 40-mile bike ride that day. So much of this trail curves along the Root River, which makes for beautiful riding.

Douglas State Trail

Nice ride

June, 2024 by djmmsherman

We're from the Twin Cities and parked in Pine Island to ride south toward Rochester. Trailhead in Pine Island is nice with restrooms, playground, wooded with asphalt path winding through. Early in the trail, cross the Zumbro River. Nice tree canopy for most of the ride. Missed taking the underpass (trail wasn't marked) and rode about half a mile before we turned around. Back on the trail through lovely rural Minnesota. Did about 13 miles and turned around for a total ride of about 26 miles. Trail in great shape overall and nice ride.

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