Winona Trails and Maps

184 Reviews

Looking for the best trails around Winona?

Find the top rated trails in Winona, whether you're looking an easy walking path or a long bike trail, you'll find what you're looking for. Click on a trail below to find trail descriptions, trail maps, photos, and reviews.

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Activities
Length
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12 Results
Activities
Length
Surfaces
Type

Buffalo River State Trail

36.4 mi
State: WI
Ballast, Crushed Stone

Chippewa River State Trail

38.5 mi
State: WI
Asphalt

Douglas State Trail

12.5 mi
State: MN
Asphalt

Douglas-Cascade Trail

2 mi
State: MN
Asphalt

Elroy-Sparta State Trail

33.8 mi
State: WI
Crushed Stone

Great River Ridge State Trail

13 mi
State: MN
Asphalt, Crushed Stone

Great River State Trail

24 mi
State: WI
Crushed Stone

Harmony-Preston Valley State Trail

18 mi
State: MN
Asphalt

La Crosse River State Trail

21 mi
State: WI
Crushed Stone

Red Cedar State Trail

14.5 mi
State: WI
Crushed Stone

Root River State Trail

42 mi
State: MN
Asphalt

Zumbro South Trail

9.9 mi
State: MN
Asphalt
Trail Image Trail Name States Length Surface Rating
The Buffalo River State Trail connects the towns of Fairchild and Mondovi along US 10 in scenic central Wisconsin. Although the rail-trail closely follows the Buffalo River, the winding waterway is...
WI 36.4 mi Ballast, Crushed Stone
The 30.4-mile Chippewa River State Trail kicks off at the confluence of the Eau Claire and Chippewa Rivers in downtown Eau Claire’s Phoenix Park, where visitors can access a walking labyrinth,...
WI 38.5 mi Asphalt
The Douglas State Trail occupies the railbed of the former Chicago Great Western Railway corridor between the cities of Rochester and Pine Island. Several of the concrete obelisk railroad mile markers...
MN 12.5 mi Asphalt
The Douglas-Cascade Trail extends 2 miles southeast towards downtown Rochester from the southern terminus of the Douglas State Trail. The paved trail, a portion of which follows the former Chicago...
MN 2 mi Asphalt
Utter darkness is as much a part of the scenery along the Elroy-Sparta State Trail as the views of the rolling hills and farmland. That’s because visitors pass through three hand-dug railroad tunnels...
WI 33.8 mi Crushed Stone
The Great River Ridge State Trail runs for 13 miles between County Road 9 just north of Eyota and Third Street Southwest just north of Wabasha Street in the town of Plainview, which serves as the...
MN 13 mi Asphalt, Crushed Stone
The Great River State Trail is named for the Mississippi River, but Ol’ Man River stays mostly out of sight if you follow this 24-mile trail through river marshes, wildlife preserves, hardwood...
WI 24 mi Crushed Stone
The Harmony–Preston Valley State Trail runs 18 miles on a north-south line between the town of Harmony and the Root River State Trail, which it meets between Lanesboro and Fountain. The paved trail is...
MN 18 mi Asphalt
The La Crosse River valley provides level terrain through a rugged area of western Wisconsin for the La Crosse River State Trail. This screened-limestone rail-with-trail passes through farmland,...
WI 21 mi Crushed Stone
One of Wisconsin’s earliest rail-trail conversions, the 14.5-mile Red Cedar State Trail is built on the former corridor of the Red Cedar Junction railway, which served Knapp, Stout & Co. in the...
WI 14.5 mi Crushed Stone
Along much of its route, the Root River State Trail follows the winding course of its namesake river for 42 miles through the Minnesota towns of Fountain, Lanesboro, Whalan, Peterson, Rushford, and...
MN 42 mi Asphalt
Offering nearly 10 miles of paved pathway through Rochester, the Zumbro South Trail serves as both an important transportation route and recreational destination. As the western end of the trail...
MN 9.9 mi Asphalt

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Trails by activity

Harmony-Preston Valley State Trail

MN - 18 miles

The Harmony–Preston Valley State Trail runs 18 miles on a north-south line between the town of Harmony and the Root River State Trail, which it meets between Lanesboro and Fountain. The paved trail is...

Douglas State Trail

MN - 12.5 miles

The Douglas State Trail occupies the railbed of the former Chicago Great Western Railway corridor between the cities of Rochester and Pine Island. Several of the concrete obelisk railroad mile markers...

Douglas-Cascade Trail

MN - 2 miles

The Douglas-Cascade Trail extends 2 miles southeast towards downtown Rochester from the southern terminus of the Douglas State Trail. The paved trail, a portion of which follows the former Chicago...

Red Cedar State Trail

WI - 14.5 miles

One of Wisconsin’s earliest rail-trail conversions, the 14.5-mile Red Cedar State Trail is built on the former corridor of the Red Cedar Junction railway, which served Knapp, Stout & Co. in the...

Accordion

La Crosse River State Trail

WI - 21 miles

The La Crosse River valley provides level terrain through a rugged area of western Wisconsin for the La Crosse River State Trail. This screened-limestone rail-with-trail passes through farmland,...

Elroy-Sparta State Trail

WI - 33.8 miles

Utter darkness is as much a part of the scenery along the Elroy-Sparta State Trail as the views of the rolling hills and farmland. That’s because visitors pass through three hand-dug railroad tunnels...

Root River State Trail

MN - 42 miles

Along much of its route, the Root River State Trail follows the winding course of its namesake river for 42 miles through the Minnesota towns of Fountain, Lanesboro, Whalan, Peterson, Rushford, and...

Zumbro South Trail

MN - 9.9 miles

Offering nearly 10 miles of paved pathway through Rochester, the Zumbro South Trail serves as both an important transportation route and recreational destination. As the western end of the trail...

Great River Ridge State Trail

MN - 13 miles

The Great River Ridge State Trail runs for 13 miles between County Road 9 just north of Eyota and Third Street Southwest just north of Wabasha Street in the town of Plainview, which serves as the...

Chippewa River State Trail

WI - 38.5 miles

The 30.4-mile Chippewa River State Trail kicks off at the confluence of the Eau Claire and Chippewa Rivers in downtown Eau Claire’s Phoenix Park, where visitors can access a walking labyrinth,...

Zumbro South Trail

MN - 9.9 miles

Offering nearly 10 miles of paved pathway through Rochester, the Zumbro South Trail serves as both an important transportation route and recreational destination. As the western end of the trail...

Great River Ridge State Trail

MN - 13 miles

The Great River Ridge State Trail runs for 13 miles between County Road 9 just north of Eyota and Third Street Southwest just north of Wabasha Street in the town of Plainview, which serves as the...

Douglas State Trail

MN - 12.5 miles

The Douglas State Trail occupies the railbed of the former Chicago Great Western Railway corridor between the cities of Rochester and Pine Island. Several of the concrete obelisk railroad mile markers...

Red Cedar State Trail

WI - 14.5 miles

One of Wisconsin’s earliest rail-trail conversions, the 14.5-mile Red Cedar State Trail is built on the former corridor of the Red Cedar Junction railway, which served Knapp, Stout & Co. in the...

Accordion

Chippewa River State Trail

WI - 38.5 miles

The 30.4-mile Chippewa River State Trail kicks off at the confluence of the Eau Claire and Chippewa Rivers in downtown Eau Claire’s Phoenix Park, where visitors can access a walking labyrinth,...

Elroy-Sparta State Trail

WI - 33.8 miles

Utter darkness is as much a part of the scenery along the Elroy-Sparta State Trail as the views of the rolling hills and farmland. That’s because visitors pass through three hand-dug railroad tunnels...

Root River State Trail

MN - 42 miles

Along much of its route, the Root River State Trail follows the winding course of its namesake river for 42 miles through the Minnesota towns of Fountain, Lanesboro, Whalan, Peterson, Rushford, and...

Great River State Trail

WI - 24 miles

The Great River State Trail is named for the Mississippi River, but Ol’ Man River stays mostly out of sight if you follow this 24-mile trail through river marshes, wildlife preserves, hardwood...

Douglas-Cascade Trail

MN - 2 miles

The Douglas-Cascade Trail extends 2 miles southeast towards downtown Rochester from the southern terminus of the Douglas State Trail. The paved trail, a portion of which follows the former Chicago...

Buffalo River State Trail

WI - 36.4 miles

The Buffalo River State Trail connects the towns of Fairchild and Mondovi along US 10 in scenic central Wisconsin. Although the rail-trail closely follows the Buffalo River, the winding waterway is...

La Crosse River State Trail

WI - 21 miles

The La Crosse River valley provides level terrain through a rugged area of western Wisconsin for the La Crosse River State Trail. This screened-limestone rail-with-trail passes through farmland,...

Harmony-Preston Valley State Trail

MN - 18 miles

The Harmony–Preston Valley State Trail runs 18 miles on a north-south line between the town of Harmony and the Root River State Trail, which it meets between Lanesboro and Fountain. The paved trail is...

Douglas State Trail

MN - 12.5 miles

The Douglas State Trail occupies the railbed of the former Chicago Great Western Railway corridor between the cities of Rochester and Pine Island. Several of the concrete obelisk railroad mile markers...

Elroy-Sparta State Trail

WI - 33.8 miles

Utter darkness is as much a part of the scenery along the Elroy-Sparta State Trail as the views of the rolling hills and farmland. That’s because visitors pass through three hand-dug railroad tunnels...

Douglas-Cascade Trail

MN - 2 miles

The Douglas-Cascade Trail extends 2 miles southeast towards downtown Rochester from the southern terminus of the Douglas State Trail. The paved trail, a portion of which follows the former Chicago...

Red Cedar State Trail

WI - 14.5 miles

One of Wisconsin’s earliest rail-trail conversions, the 14.5-mile Red Cedar State Trail is built on the former corridor of the Red Cedar Junction railway, which served Knapp, Stout & Co. in the...

Accordion

La Crosse River State Trail

WI - 21 miles

The La Crosse River valley provides level terrain through a rugged area of western Wisconsin for the La Crosse River State Trail. This screened-limestone rail-with-trail passes through farmland,...

Great River State Trail

WI - 24 miles

The Great River State Trail is named for the Mississippi River, but Ol’ Man River stays mostly out of sight if you follow this 24-mile trail through river marshes, wildlife preserves, hardwood...

Root River State Trail

MN - 42 miles

Along much of its route, the Root River State Trail follows the winding course of its namesake river for 42 miles through the Minnesota towns of Fountain, Lanesboro, Whalan, Peterson, Rushford, and...

Zumbro South Trail

MN - 9.9 miles

Offering nearly 10 miles of paved pathway through Rochester, the Zumbro South Trail serves as both an important transportation route and recreational destination. As the western end of the trail...

Great River Ridge State Trail

MN - 13 miles

The Great River Ridge State Trail runs for 13 miles between County Road 9 just north of Eyota and Third Street Southwest just north of Wabasha Street in the town of Plainview, which serves as the...

Harmony-Preston Valley State Trail

MN - 18 miles

The Harmony–Preston Valley State Trail runs 18 miles on a north-south line between the town of Harmony and the Root River State Trail, which it meets between Lanesboro and Fountain. The paved trail is...

Buffalo River State Trail

WI - 36.4 miles

The Buffalo River State Trail connects the towns of Fairchild and Mondovi along US 10 in scenic central Wisconsin. Although the rail-trail closely follows the Buffalo River, the winding waterway is...

Chippewa River State Trail

WI - 38.5 miles

The 30.4-mile Chippewa River State Trail kicks off at the confluence of the Eau Claire and Chippewa Rivers in downtown Eau Claire’s Phoenix Park, where visitors can access a walking labyrinth,...

Recent Trail Reviews

Elroy-Sparta State Trail

Closed in September 2018

September, 2018 by bruceamiller@comcast.net

This trail was closed in September by the Wisconsin DNR, due to mudslides and other trail conditions caused by heavy rains.

Great River State Trail

A wet ride past boring views

September, 2018 by bruceamiller@comcast.net

In September 2018 a friend and I biked the trail from Trempealeau National Wildlife Refuge to Onalaska and back. Unfortunately it rained heavily all morning, so our ride south was nearly all in 1-2 inches of water. Coming back later in the day, the puddles were mostly gone thanks to sandy soil. Other than skirting the town of Trempealeau, the view is nearly all Mississippi backwaters, restful and boring. We hoped to see migratory birds but were too early. BE CAREFUL on the bridges: the wooden patches sometimes are at an angle and have nails sticking up. Also, there are no bathrooms or businesses north of the town of Trempealeau.

La Crosse River State Trail

Liked the mix of farmland and small towns

September, 2018 by bruceamiller@comcast.net

In September 2018 a friend and I biked the trail from Sparta to La Crosse and back. The Sparta trailhead has good bathrooms and a helpful lady in the Chamber of Commerce office in the former depot. Although the 400 and Elroy-Sparta State Trails are closed due to mudslides, this trail was open and OK.
We liked the mix of farmland and small towns (recommend West Salem for lunch), nearly level trail, decent trail surface of crushed limestone, and train activity parallel to the trail
We didn't like the constant traffic noise from Interstate 90, mostly at a distance but crosses over several times.
The La Crosse trailhead has bathrooms and parking but is several miles from restaurants.

Accordion

Zumbro South Trail

Great trail, needs betters signs for loop

September, 2018 by cubby7778

Needs better signs for the L 10 LOOP. had a great time with the dog.

Harmony-Preston Valley State Trail

Aug 21 harmony

August, 2018 by elliott4

This trail could use some tlc, volunteer with asphalt repair equipment. Lots of bumps and holes, reason is 80% canopy ride. This ride is a workout but thats good sometimes. If its hot canopy would be great and i bet leaves are beautiful come October

Root River State Trail

Preston to Houston Campout

August, 2018 by elliott4

Aug 21,Road Preston to Houston, stopped for Italian in Rushford ($$). Setup tent at Harmony Trailhead,found American Legion open ( very nice staff and customers, well lit, marble bar top), county ampground level and great showerhouse $20 for spot, little unusual sign requested $ for shower i assume it was for people who don't camp. Aug 22, Great coffee shop breakfadt place on main st. Houston, we also stopped Rushford for more coffee on ride. Pie place closed tue/wed Whalen. Trail 80% canopy ride, wide and good condition. Actually road harmony to houston 55 miles 600' climb, return is 55 and 1200' climb.

Root River State Trail

It Doesn't Get Any Better Than This!

August, 2018 by gregoryscottharrison

I've ridden rail trails all over the country, and I would have to say that this one is at the top of my list. The riding is beautiful and peaceful along the entire trail, the surface is perfectly paved, the scenery is gorgeous, and the towns that you ride through are all "Norman Rockwell-esqe." The proximity to towns - all about 5 - 8 miles apart - are what really make this a special trail. You can get anything you want during your ride......an ice cold beer, a root beer float, a delicious breakfast/lunch/dinner, and if you decide you want to stay in a town you can book a room at one of the many beautiful inns. The other thing that puts this trail to the top are the people you will interact with on the trail and in the towns. "Minnesota Nice" is a popular catchphrase around here and it's more than just a catchy slogan. People around here are happy, generous, kind and helpful. Do yourself a favor and schedule a week-long vacation in the Root River Valley so you can enjoy this amazing network of bike paths.

Elroy-Sparta State Trail

A long time ago

July, 2018 by okpilak20061

I rode this trail, and much more as part of a several hundred mile bicycle trip in the early 1970's, and again just this portion several years later. I did not dismount going through the tunnels, just kept my ears sharp listening to the dripping water to maintain my center of the trail; no flashlight either. The tunnel that makes the bend was the real challenge. I remember that a farmer had put a soft drink machine at the edge of his farm along the trail, and I wondered how much the electric cable must had cost him.

It was easy pedaling and the best part was it was free. Seeing now that there is a charge, and not a trivial one, I would never return. The surface seemed mostly packed shale.

The businesses at each end of the trail were just getting started then and there was very little traffic on the trail. There seemed a hint that they expected snowmobiles to be the biggest draw at that time, with winter use being the major use.

The second time I rode it was in the Fall, and the colors were amazing, and it was a wonderful time.

Elroy-Sparta State Trail

Poorly maintained for a fee based trail

July, 2018 by salesjer

This is a nice trail but needs to be better maintained, especially when they are charging $5 per day to ride the trail. Four of us rode July 21, 2018 (Saturday) and 2 trees were down between Wilton and Elroy. We had to lift our bikes over and then climb over a large tree blocking the path. Another tree was down but you could get around it by going in the ditch. People with bike trailers for children would not be able to pass. Other areas had a lot of mud on the trail. The tunnels are very cool but it is disappointing that you have to walk your bike, one is 3/4 mile long and that really interrupts the flow of a ride. Again, I think if the surface in the tunnels was better maintained it would be safe to ride through.

Red Cedar State Trail

Memorable first ride

July, 2018 by bobsiewert

I echo all of the previous reviews. Absolutely breathtaking views on my fat bike of both the Red Cedar and Chippewa Rivers. Trail conditions were overall great however keep your eyes open for unexpected gopher holes. The path is fairly wide at all points. Some of the people on road bikes mentioned they had a bumpy ride. I started at Meridean on the CRST, biked up to Menomonie (nice trailhead welcoming center), back down the RCST, proceeded to Durand and then back to Meridean for a total of 51 miles. There were nice logical scenic spots to take a break along the way with clean restrooms, water and tire pumps. There were deer along several spots along the trail. While on my ride, a DNR worker with a polite disposition was busily performing maintenance on a culvert on the trail...good to see. BE SURE TO PACK BUG SPRAY if you plan on stopping for more than 10-15 seconds on the lower end of the trail. Definite 5* must ride, scenic and peaceful trail.

Red Cedar State Trail

Bad bugs!!

July, 2018 by mbollom

Fabulous trail—beautiful and peaceful. But my wife and I suffered our second worst bug attack of our 50 years—mosquitos and and deer flies. Bring spray and be ready to ride quickly with no breaks.

Elroy-Sparta State Trail

Very cool trail

July, 2018 by irmaiden

I just spent the last 2 days riding this trail. We started out at the Kendall depot on Monday(it is closed on Monday and Tuesday) so I didn't get a chance to go inside. We rode 3 1/2 miles to the first tunnel. That was amazing to see as I rode towards it and started to feel the cool air coming from it. Very cool tunnel. After the 1st tunnel it was a pretty good downhill ride. I think it was about 8 1/2 miles to the next tunnel.Overall we turned around at the 12 mile point and went back to the car in Kendall. Coming back was tougher as it got hotter, and it was more uphill. I also got a leak in my back tire with 6-7 miles to go. I had to use my mini pump to fill it 3 different times to make it back. I changed the inner tube later that night at the hotel. After the ride we got in the car and drove to Sparta. We stayed at a nice hotel(Super 8) and had a great dinner at Slice of Chicago. We woke up and rode the Tail starting in Sparta. It was a gradual uphill ride for 9 miles to get to the 3rd tunnel. It was a long tunnel and yes it was dripping quite a bit. You get a little wet but not drenched at all. I had a great flashlight attached to my bike that worked great. We tuned around at the 11 mile mark and had a good downhill ride back to the Sparta depot. Right before tunnel 3 we stopped and talked to the older guy who sells ice cream and flashlights out of a small shack. What a friendly nice guy. Overall this trip worked out great with biking over two days. The trail, and the tunnels,and the countryside were beautiful. The only reason I gave this trail 4 stars was because it isn't paved. I had no problem with the trail surface except at some points it is a little narrow,but well compacted. It was about 2 1/2 hours from Milwaukee,and I will definitely be back to ride this some more. It was a really fun little trip. If you haven't been to this trail,you should make a trip out here.

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