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greenBlue Cherry Hill Plowline Trail

  3.7 ( 6 ) Favorite

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6.1 mile 9.8 kilometer loop
15% Singletrack


Ascent: 540' 165 m
Descent: -514' -157 m
High: 1,181' 360 m
Low: 1,028' 313 m


Avg Grade: 3% (2°)
Max Grade: 14% (8°)


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Trail shared by Scott Sherman

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A beautiful ride across the top of the Winona's beautiful bluffs, overlooking the Mississippi River.

Scott Sherman

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Features -none-

This trail is for winter use only when snow covered.


This trail is broken into 4 sections, with a main road that runs down the center of the quadrants. Riding the trail, you'll encounter beautiful vistas, long-established goat prairies, deciduous and coniferous forests, as well as an abundance of wildlife.

These trails are for non-motorized uses only (hiking, bicycling, horseback riding, and cross-country skiing). Both loops generally follow the edge of the woods, or the plow line, as they go around the ridge. Both rise and fall with the terrain, giving them a "easy/Intermediate" rating for mountain biking. The north loop goes out to scenic overlooks of Stockton Valley and the Mississippi River Valley.

Directions and overview are available at the Minnesota DNR website.

These trails are maintained by DNR and Winona Area Mountain Bikers. WAMB gained approval for 9 miles of singletrack in 2014. As of now, 1+ mile of singletrack are accessible at the end of the main center road and quadrant 3.

Need to Know

There are two trails that lead up to Cherry Hill. Both these trails would be considered intermediate due to the grade and elevation rise. Cherry Hill is roller groomed in the winter for fat-biking.


There are two different routes to Cherry Hill. The Hidden Valley route is more easily accessible from Winona proper.

One is from the Hidden Valley Trailer Court up County Road 6. Head up the County Road 6 (gravel) road. There is a paved road that heads up to the water tower. Turn left on the dirt road at this intersection. Follow this up to the top of the bluff, where you'll see locked gates. Keep heading up the hill to the right. This will put you at the trailhead. There is a current map there.

The other access is up from the DNR parking lot on the "backside" of the bluff. The parking lot is at the end of Brook Dr, accessible off of County Road 23. From the parking lot, ride up the gravel road to the top of the bluff. At the top of the climb, you'll encounter locked gates. Head up the hill to the left and you'll encounter the trailhead.

This trail is broken into 4 sections, with a main road that runs down the center of the quadrants. The normal route is counter-clockwise around the 4 quadrants. Towards the end of the main road, there is an access to the newly built singletrack. Currently, there is 1+ mile of singletrack that will dump you back onto quadrant 3. These access points are temporary as more trail is being built.

Cherry Hill is groomed in the winter for fat biking.

History & Background

The Bronk Management Unit is named for Leon A. Bronk, from whom the property was purchased in 1969. This 761-acre unit straddles the ridge between Stockton Valley and the Mississippi River. The slopes of the ridge rise 500 feet above the surrounding valleys, providing numerous scenic overlooks.


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Jun 24, 2018
Kevin Brom
Jan 6, 2018
Paul Niebuhr
Made the mistake of taking the trail from the first parking lot on Brook Dr. Pretty impossible climbing in the snow, really steep. 7.2mi
Nov 19, 2017
Kevin Brom

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Trail Ratings

  3.7 from 6 votes


in Winona


  3.7 from 6 votes
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65 Views Last Month
1,826 Since Jun 11, 2015
Easy/Intermediate Easy/Intermediate

As a bigginer this track is perfect. I brought one son that is a beginner and we had to walk some of the inital climb but the rest he could handle. I am bringing a different son that has never been mountain biking before. I am sure he will have to walk some of the inital climb too. I will be trying other tracks with a higher dificult soon. Sep 17, 2016

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