Winona, MN Walking Trails and Maps

313 Reviews

Looking for the best Walking trails around Winona?

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

  • Relevance
  • Name
  • Length
  • Most Popular
Activities
Length
Surfaces
Type
61 Results
Activities
Length
Surfaces
Type

Bear Creek Cutoff Trail

1.04 mi
State: MN
Asphalt

Cascade Lake Trail

1.4 mi
State: MN
Asphalt

Chippewa River State Trail

30.4 mi
State: WI
Asphalt, Boardwalk, Cinder, Concrete, Gravel

Douglas State Trail

12.5 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

Jim Asfoor Trail

1.3 mi
State: WI
Asphalt

La Crosse River State Trail

21 mi
State: WI
Crushed Stone

Pammel Creek Trail

2 mi
State: WI
Asphalt

Red Cedar State Trail

14.8 mi
State: WI
Crushed Stone

Root River State Trail

42.1 mi
State: MN
Asphalt

Zumbro South Trail

6.5 mi
State: MN
Asphalt

Great River State Trail

27.6 mi
State: WI
Crushed Stone

Harmony-Preston Valley State Trail

18 mi
State: MN
Asphalt

Buffalo River State Trail

36.4 mi
State: WI
Ballast, Crushed Stone

Swift Creek Trail

1.9 mi
State: WI
Asphalt

40th Street Bike Path

1.5 mi
State: MN
Asphalt

48th Street Bike Path

2.1 mi
State: MN
Asphalt

50th Avenue Bike Path

2.5 mi
State: MN
Asphalt, Concrete
Accordion

Badger Hills Bike Path

1.8 mi
State: MN
Asphalt

Bandel Road Path

0.9 mi
State: MN
Asphalt

Bear Creek Trail (MN)

3.4 mi
State: MN
Asphalt

Bud Hendrickson Nature Trail

1.2 mi
State: WI
Asphalt

Cascade Creek Trail

3.6 mi
State: MN
Asphalt

Civic Center Trail

1.2 mi
State: MN
Asphalt

Douglas-Cascade Trail

2 mi
State: MN
Asphalt

East 55th Street Path

1.5 mi
State: MN
Asphalt

East Circle Drive Bike Path

1.6 mi
State: MN
Asphalt

Elton Hills Run Trail

0.6 mi
State: MN
Asphalt

Essex Park Trail

1.1 mi
State: MN
Asphalt

Flyway Trail

3.2 mi
State: MN, WI
Asphalt, Boardwalk, Concrete, Crushed Stone

Foster-Arend Trail

1.7 mi
State: MN
Asphalt

Foundation Trail

3.19 mi
State: WI
Asphalt

Graham Park Trail

1.1 mi
State: MN
Asphalt

Grand Crossing Trail

1 mi
State: WI
Asphalt

Hart Farms Trail

0.7 mi
State: MN
Asphalt

John Wellner Memorial Trail

3.3 mi
State: MN
Asphalt

Lincolnshire Trail

1.5 mi
State: MN
Asphalt

Marion Road Bike Path

1.5 mi
State: MN
Asphalt

Mayowood Bike Path

0.7 mi
State: MN
Asphalt

Meadow Park Bike Path

1.8 mi
State: MN
Asphalt

North Frontage Trail

3.3 mi
State: MN
Asphalt, Concrete

Overland Drive Trail

1.6 mi
State: MN
Asphalt

Quarry Hill Family Trail

0.61 mi
State: MN
Asphalt

Ridge View Manor Trail

1 mi
State: MN
Asphalt

Salem Road Bike Path

1.5 mi
State: MN
Asphalt

South Frontage Bike Path

1 mi
State: MN
Asphalt

Southern Woods Trail

0.75 mi
State: MN
Asphalt

St. Bridgets Bike Path

0.75 mi
State: MN
Asphalt

Summit Pointe Trail

0.9 mi
State: MN
Asphalt

The Gardens Trail

1.1 mi
State: MN
Asphalt

Valleyhigh Road Bike Path

0.7 mi
State: MN
Asphalt

Vietnam Veterans Trail

0.9 mi
State: WI
Asphalt

Wagon Wheel Trail

0.8 mi
State: MN
Crushed Stone, Gravel

West 55th Street Path

1.3 mi
State: MN
Asphalt

West Circle Drive Bike Path

4.1 mi
State: MN
Asphalt

White Oaks Trail

1.5 mi
State: MN
Asphalt

Willow Trail

0.6 mi
State: WI
Asphalt

Zumbro North Trail

5.1 mi
State: MN
Asphalt
Trail Image Trail Name States Length Surface Rating
The Bear Creek Cutoff Trail serves as a short connector trail, allowing cyclists and pedestrians access to and from the southern end of the Bear Creek Trail. The asphalt pathway spans from 11th Avenue...
MN 1.04 mi Asphalt
Offering a pleasant path along the southern side of Cascade Lake, the Cascade Lake Trail allows cyclists and pedestrians to explore the grounds around the lakeshore and Cascade Lake Park, home to a...
MN 1.4 mi Asphalt
Overview The 30.4-mile Chippewa River State Trail runs between Eau Claire and Durand, Wisconsin.  Snowmobiles are permitted between Porterville Road and Durand. NOTE: A State Trail Pass ($25...
WI 30.4 mi Asphalt, Boardwalk, Cinder, Concrete, Gravel
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
Note: The three tunnels on the trail close from Nov. 1 to April 30 each year. Overview Three hand-dug tunnels along the Elroy-Sparta State Trail make utter darkness as much a part of the scenery...
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 Jim Asfoor Trail is a paved hike-and-bike trail within La Crosse's marshlands. The trail is part of the Marsh Trail Network, cluster of paved and unpaved trails occupying the thousand-acre wetland...
WI 1.3 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
The Pammel Creek Trail is a paved path in La Crosse. The trail mostly follows the alignment of the Pammel Creek channel. The trail travels through residential areas in the south part of La Crosse,...
WI 2 mi Asphalt
Overview One of Wisconsin’s earliest rail-trail conversions, the 14.8-mile Red Cedar State Trail is built on the former corridor of the Red Cedar Junction railway, which served Knapp, Stout & Co....
WI 14.8 mi Crushed Stone
Overview 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,...
MN 42.1 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 6.5 mi Asphalt
Overview The Great River State Trail is named for the Mississippi River, but Ol’ Man River stays mostly out of sight if you follow this 27.6-mile trail through river marshes, wildlife preserves,...
WI 27.6 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 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 Swift Creek Trail combines a trail segment running the length of Isle la Plume and a walking trail that was the initiative of staff of the Gundersen Health System in La Crosse. The trail begins in...
WI 1.9 mi Asphalt
The 40th Street Bike Path is an asphalt sidepath trail that follows its namesake roadway through a lightly developed stretch of southern Rochester, coasting over rolling hills and the edge of woods to...
MN 1.5 mi Asphalt
Running for over two miles over gentle hills, highway exit ramps, and creeks and fields, the 48th Street Bike Path is an asphalt sidepath trail that provides a route for cyclists and pedestrians in...
MN 2.1 mi Asphalt
On the northwestern edge of Rochester, the 50th Avenue Bike Path runs across over two miles of rolling hills, an asphalt sidepath trail that follows the west side of the road as it passes through open...
MN 2.5 mi Asphalt, Concrete
Named in the memory of Arianna Celeste Macnamara, a 7-year old girl who was tragically killed when she was struck by a car while crossing a nearby intersection, the Arianna Celeste Macnamara Memorial...
MN 0.37 mi Concrete
Accordion
The Badger Hills Bike Path is a suburban sidepath trail that travels along the side of 41st Street and Badger Hills Drive in northern Rochester. While not much to look at, this asphalt pathway...
MN 1.8 mi Asphalt
The Bandel Road Path is an asphalt sidepath that runs primarily in a utility corridor along the side of Bandel Road in northern Rochester. The pathway provides an alternative option for cyclists to...
MN 0.9 mi Asphalt
The great thing about Rochester's extensive trail system is that it gives you the best of both words: not only are the trails great for recreation out in nature, they are also convenient for commuters...
MN 3.4 mi Asphalt
This trail and bike-ped bridge are named for a La Crosse resident and trail lover, whose independent efforts to create a walking path in the 1950s would pave the way for this trail. The hard surface...
WI 1.2 mi Asphalt
Linking some of Rochester's most popular parks and recreation sites, the Cascade Creek Trail follows its namesake creek for over three miles, from Manorwoods Lake and Cascade Lake in the west, to the...
MN 3.6 mi Asphalt
Rochester, Minnesota is home to a whole host of excellent multi-use pathways and trails, giving cyclists and pedestrians ample opportunity to explore the outdoors and get in plenty of safe recreation...
MN 1.2 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
The East 55th Street Path is an asphalt sidepath that runs along the side of 55th Street through a suburban stretch of northern Rochester, providing a key connection in the area's bike and pedestrian...
MN 1.5 mi Asphalt
The East Circle Drive Bike Path is an asphalt sidepath in northern Rochester that helps provide a connection between the John Wellner Memorial Trail and the Zumbro North Trail, two key components of...
MN 1.6 mi Asphalt
A short offshoot of the longer Zumbro North Trail, the Elton Hills Run Trail provides a quick and convenient connection to the neighborhoods to the west of the river, as well as the small local park...
MN 0.6 mi Asphalt
The Essex Park Trail is a short, paved trail that connects neighborhoods in northern Rochester with the verdant grounds of Essex Park, home to playgrounds and plenty of open recreation space. The...
MN 1.1 mi Asphalt
Flyway Trail is a community-driven startup committed to building a world-class trail in Buffalo County. The long-term goals for this project aim to increase community connectivity, support economic...
MN, WI 3.2 mi Asphalt, Boardwalk, Concrete, Crushed Stone
The Foster-Arend Trail helps connect residents in northern Rochester with the rest of the city's network of trails and bike paths, and leads into Foster-Arend Park, a popular local park that offers...
MN 1.7 mi Asphalt
The picturesque Foundation Trail encircles the city of Black River Falls Wisconsin. It is a paved asphalt 10-ft wide trail that features bridges, benches, picnic tables and lights. It meanders around...
WI 3.19 mi Asphalt
Paralleling South Broadway and 16th Street in the heart of Rochester, the Graham Park Trail provides a nice alternative to the busy roadways for cyclists and pedestrians, leading trail users along a...
MN 1.1 mi Asphalt
The Grand Crossing Trail is a north-south trail located in La Crosse's marshlands. The hard-surface trail begins on River Valley Drive and extends south to Myrick Park Drive. The trail offers an...
WI 1 mi Asphalt
A short sidepath trail that runs through a neighborhood in the southern reaches of Rochester, the Hart Farms Trail offers a pleasant asphalt path for local residents. Sharing the roadside with a row...
MN 0.7 mi Asphalt
This multiuse trail is named in honor of a man who worked to make sure Rochester residents had safe places to walk and cycle. John Wellner was the city's infrastructure manager for 18 years, during...
MN 3.3 mi Asphalt
The Lincolnshire Trail is an asphalt pathway that shoots off from the longer Douglas State Trail, providing a short spur that gives cyclists and pedestrians access to the Lincolnshire-Arbor Glen...
MN 1.5 mi Asphalt
Running alongside Marion Road in southern Rochester, the Marion Road Bike Path provides an asphalt sidepath trail for cyclists and pedestrians to use - together with the Bear Creek Trail and the...
MN 1.5 mi Asphalt
A neighborhood offshoot of the longer Zumbro South Trail, the Mayowood Bike Path is an asphalt sidepath trail that parallels Mayowood Road in southern Rochester. The trail is relatively flat, running...
MN 0.7 mi Asphalt
Running through the Meadow Park neighborhood in southern Rochester, the Meadow Park Bike Path provides a convenient connection for residents of the nearby neighborhoods to reach popular local parks...
MN 1.8 mi Asphalt
In Winona County, the Mississippi River Regional Trail runs parallel to US 61/14 and the rail line for almost three miles. The trail becomes a bike lane at the southern endpoint on US 14/61. 
MN 2.9 mi Asphalt
Spanning over three miles along the side of Highway 52 as it runs through Rochester, the North Frontage Trail provides a space for cyclists and pedestrians alongside all the nearby automotive traffic....
MN 3.3 mi Asphalt, Concrete
One of Rochester's many suburban sidepath trails, the Overland Drive Trail runs along a roadside near the northern limits of the city. Passing over rolling hills and through the edges of residential...
MN 1.6 mi Asphalt
Located within the wooded acres of Quarry Hill Park, a popular recreation destination in Rochester, the Quarry Hill Family Trail is a flat, paved multi-use trail that serves as a connection in the...
MN 0.61 mi Asphalt
The Ridge View Manor Trail is a short trail that branches off from the Douglas State Trail, connecting the popular recreation pathway with growing suburban developments in northwestern Rochester. The...
MN 1 mi Asphalt
The Salem Road Bike Path is an asphalt sidepath trail that runs along Salem Road and West Frontage Road in a pretty, suburban section of southern Rochester. The pathway picks up where the West Circle...
MN 1.5 mi Asphalt
Connecting neighborhoods and trails in southern Rochester with the important Cascade Creek Trail corridor, the South Frontage Bike Path serves a key role in the off-road transportation network,...
MN 1 mi Asphalt
The Southern Woods Trail is a short, paved trail that runs through a pretty section of suburban southern Rochester. The trail starts in the north where the 48th Street Bike Path crosses over Willow...
MN 0.75 mi Asphalt
A straightforward asphalt sidepath trail, the St. Bridgets Bike Path runs along the side of its namesake roadway in southern Rochester, in a residential and commercial pocket just off Highway 63....
MN 0.75 mi Asphalt
A short neighborhood trail that runs through Summit Pointe Park in northwest Rochester, the Summit Pointe Trail provides a great outlet for cyclists and pedestrians to get some exercise and outdoor...
MN 0.9 mi Asphalt
Forming a circuit around a suburban development in southern Rochester, The Gardens Trail offers a dose of natural beauty and recreation just off of the busy nearby highway. The trail branches off from...
MN 1.1 mi Asphalt
The Valleyhigh Road Bike Path is a paved asphalt sidepath trail that provides a short connection between several paths in Rochester's system of multi-use trails. The western end marks the beginning of...
MN 0.7 mi Asphalt
La Crosse's Marsh Trail Network is a collection of paved and unpaved trails occupying the 1000 acre wetland where the La Crosse River meets the Mississippi River. The marsh, which lies minutes from...
WI 0.9 mi Asphalt
The Wagon Wheel Trail runs for less than a mile through the Upper Mississippi National Wildlife and Fish Refuge. Blue Lake is just south of the trail, which has a crushed gravel surface suitable for...
MN 0.8 mi Crushed Stone, Gravel
Covering a residential section of northwestern Rochester, the West 55th Street Path helps connect neighborhood residents with the rest of Rochester's expansive trail network, including the lovely and...
MN 1.3 mi Asphalt
A suburban sidepath trail that runs along the western edge of Rochester, Minnesota, the West Circle Drive Bike Path provides an important link in the city's expanding trail network. The path runs...
MN 4.1 mi Asphalt
Located in northwestern Rochester, the White Oaks Trail provides a safe and pleasant connection for residents to access White Oaks Park and the Douglas State Trail, one of the area's premier...
MN 1.5 mi Asphalt
La Crosse's marshlands sit on a thousand acres in the heart of the city. The wetlands occur where the La Crosse and Mississippi rivers meet. The Marsh Trail Network is a cluster of paved and unpaved...
WI 0.6 mi Asphalt
Stretching for over five miles along the south fork of the Zumbro River, the Zumbro North Trail acts as part of the backbone of the city of Rochester's fantastic network of trails and bike paths,...
MN 5.1 mi Asphalt

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

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.

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.

Find Nearby City trails

Register for free!

Register for free with TrailLink today!

We're a non-profit all about helping you enjoy the outdoors
  • View over 40,000 miles of trail maps
  • Share your trail photos
  • Save your own favorite trails
  • Learn about new trails near you
  • Leave reviews for trails
  • Add new and edit existing trails

Get the Free TrailLink App

The trail is always better with TrailLink

Scan the QR code to get TrailLink on your phone

Explore by City

Explore by City

Explore by Activity

Explore by Activity

Log in to your account to:

  • View trail paths on the map
  • Save trails to your account
  • Add trails, edit descriptions
  • Share photos
  • Add reviews

Log in with Google

Log in with Apple

OR

Register for free!

Join TrailLink (a non-profit) to view more than 40,000 miles of trail maps and more!

Register with Google

Register with Apple

OR

Your account has been deleted.