Chester Trails and Maps

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Find the top rated trails in Chester, 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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  • Length
Activities
Length
Surfaces
Type
16 Results
Activities
Length
Surfaces
Type

Blazing Star State Trail

6 mi
State: MN
Asphalt

Douglas State Trail

12.5 mi
State: MN
Asphalt

Douglas-Cascade Trail

2 mi
State: MN
Asphalt

Great River Ridge State Trail

13 mi
State: MN
Asphalt, Crushed Stone
Accordion

Harmony-Preston Valley State Trail

18 mi
State: MN
Asphalt

Harry Cook Nature Trail

2 mi
State: IA
Crushed Stone

NIACC Trail

2.2 mi
State: IA
Asphalt

Prairie Farmer Recreational Trail

20 mi
State: IA
Asphalt

Riverside Trail (IA)

1.2 mi
State: IA
Asphalt

Root River State Trail

42 mi
State: MN
Asphalt

Shooting Star State Trail

18.8 mi
State: MN
Asphalt

Trout Run Trail

11 mi
State: IA
Asphalt, Concrete

Wapsi-Great Western Line Trail

18.5 mi
State: IA
Asphalt, Crushed Stone

Winnebago Trail

2 mi
State: IA
Crushed Stone
Trail Image Trail Name States Length Surface Rating
The Blazing Star State Trail is located in Albert Lea, near Minnesota’s southern border. The town is known as “The Land Between the Lakes,” and the trail begins on the northern shore of one of the state’s ...
MN 6 mi Asphalt
The Charley Western Recreational Trailway provides a useful off-road route around the outer limits of Charles City. Built on the site of the former Charles City Western Railway, the trail runs along the ...
IA 4 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 Great ...
MN 2 mi Asphalt
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 agricultural ...
MN 13 mi Asphalt, 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 Harry Cook Nature Trail runs for 2 miles from the edge of the small city of Osage, Iowa to the city's public Spring Park. The trail, which opened in the early 1990s, occupies the bed of an abandoned ...
IA 2 mi Crushed Stone
Accordion
The NIACC Trail in Cerro Gordo County, Iowa, connects the campus of North Iowa Area Community College with the edge of downtown Mason City. The trail provides a convenient and safe alternative to biking ...
IA 2.2 mi Asphalt
The Prairie Farmer Rec. Trail (a.k.a. Winneshiek County Trail) was named for a radio show once broadcast throughout the Midwest. The trail occupies the right-of-way of the former Milwaukee Railroad, which ...
IA 20 mi Asphalt
Charles City's Riverside Trail runs for a little over a mile along the banks of the Cedar River, providing gorgeous views and recreational opportunities, as well as access to several city parks. Starting ...
IA 1.2 mi Asphalt
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 Houston. ...
MN 42 mi Asphalt
Shooting Star State Trail, currently 19 miles long, is an 8-foot-wide asphalt path from LeRoy (east) to Rose Creek (west). It follows an unused railroad bed on Milwaukee Road, which once stretched from ...
MN 18.8 mi Asphalt
Most of northern Iowa's Trolley Trail is a straight line paralleling both 255th St./4th Ave. and the operational trolley tracks on the other side of the road. But what the Trolley Trail may lack in variety ...
IA 6.2 mi Asphalt
Trout Run Trail forms an 11-mile loop around Decorah, providing access to many of the area's natural treasures and views of beautiful Iowa countryside. Although there are many places to hop on the trail, ...
IA 11 mi Asphalt, Concrete
The 18.5 mile long Wapsi-Great Western Line Trail follows the abandoned Chicago Great Western Railway grade between Riceville and the Iowa/Minnesota State Line. The corridor was originally built by the ...
IA 18.5 mi Asphalt, Crushed Stone
Mason City's Winnebago Trail connects MacNider Campground, East Park, residential neighborhoods and the city's municipal swimming pool with the Lime Creek Nature Center just outside city limits. Along ...
IA 2 mi Crushed Stone

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Trails by activity

Blazing Star State Trail

MN - 6 miles

The Blazing Star State Trail is located in Albert Lea, near Minnesota’s southern border. The town is known as “The Land Between the Lakes,” and the trail begins on the northern shore of one of the state’s ...

Charley Western Recreational Trailway

IA - 4 miles

The Charley Western Recreational Trailway provides a useful off-road route around the outer limits of Charles City. Built on the site of the former Charles City Western Railway, the trail runs along 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 ...

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 Great ...

Accordion

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 Great ...

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 agricultural ...

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 ...

Harry Cook Nature Trail

IA - 2 miles

The Harry Cook Nature Trail runs for 2 miles from the edge of the small city of Osage, Iowa to the city's public Spring Park. The trail, which opened in the early 1990s, occupies the bed of an abandoned ...

NIACC Trail

IA - 2.2 miles

The NIACC Trail in Cerro Gordo County, Iowa, connects the campus of North Iowa Area Community College with the edge of downtown Mason City. The trail provides a convenient and safe alternative to biking ...

Prairie Farmer Recreational Trail

IA - 20 miles

The Prairie Farmer Rec. Trail (a.k.a. Winneshiek County Trail) was named for a radio show once broadcast throughout the Midwest. The trail occupies the right-of-way of the former Milwaukee Railroad, which ...

Riverside Trail (IA)

IA - 1.2 miles

Charles City's Riverside Trail runs for a little over a mile along the banks of the Cedar River, providing gorgeous views and recreational opportunities, as well as access to several city parks. Starting ...

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 Houston. ...

Shooting Star State Trail

MN - 18.8 miles

Shooting Star State Trail, currently 19 miles long, is an 8-foot-wide asphalt path from LeRoy (east) to Rose Creek (west). It follows an unused railroad bed on Milwaukee Road, which once stretched from ...

Trolley Trail (Clear Lake/Mason City)

IA - 6.2 miles

Most of northern Iowa's Trolley Trail is a straight line paralleling both 255th St./4th Ave. and the operational trolley tracks on the other side of the road. But what the Trolley Trail may lack in variety ...

Trout Run Trail

IA - 11 miles

Trout Run Trail forms an 11-mile loop around Decorah, providing access to many of the area's natural treasures and views of beautiful Iowa countryside. Although there are many places to hop on the trail, ...

Wapsi-Great Western Line Trail

IA - 18.5 miles

The 18.5 mile long Wapsi-Great Western Line Trail follows the abandoned Chicago Great Western Railway grade between Riceville and the Iowa/Minnesota State Line. The corridor was originally built by the ...

Winnebago Trail

IA - 2 miles

Mason City's Winnebago Trail connects MacNider Campground, East Park, residential neighborhoods and the city's municipal swimming pool with the Lime Creek Nature Center just outside city limits. Along ...

Blazing Star State Trail

MN - 6 miles

The Blazing Star State Trail is located in Albert Lea, near Minnesota’s southern border. The town is known as “The Land Between the Lakes,” and the trail begins on the northern shore of one of the state’s ...

Charley Western Recreational Trailway

IA - 4 miles

The Charley Western Recreational Trailway provides a useful off-road route around the outer limits of Charles City. Built on the site of the former Charles City Western Railway, the trail runs along 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 ...

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 Great ...

Accordion

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 Great ...

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 agricultural ...

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 ...

Harry Cook Nature Trail

IA - 2 miles

The Harry Cook Nature Trail runs for 2 miles from the edge of the small city of Osage, Iowa to the city's public Spring Park. The trail, which opened in the early 1990s, occupies the bed of an abandoned ...

NIACC Trail

IA - 2.2 miles

The NIACC Trail in Cerro Gordo County, Iowa, connects the campus of North Iowa Area Community College with the edge of downtown Mason City. The trail provides a convenient and safe alternative to biking ...

Prairie Farmer Recreational Trail

IA - 20 miles

The Prairie Farmer Rec. Trail (a.k.a. Winneshiek County Trail) was named for a radio show once broadcast throughout the Midwest. The trail occupies the right-of-way of the former Milwaukee Railroad, which ...

Riverside Trail (IA)

IA - 1.2 miles

Charles City's Riverside Trail runs for a little over a mile along the banks of the Cedar River, providing gorgeous views and recreational opportunities, as well as access to several city parks. Starting ...

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 Houston. ...

Shooting Star State Trail

MN - 18.8 miles

Shooting Star State Trail, currently 19 miles long, is an 8-foot-wide asphalt path from LeRoy (east) to Rose Creek (west). It follows an unused railroad bed on Milwaukee Road, which once stretched from ...

Trolley Trail (Clear Lake/Mason City)

IA - 6.2 miles

Most of northern Iowa's Trolley Trail is a straight line paralleling both 255th St./4th Ave. and the operational trolley tracks on the other side of the road. But what the Trolley Trail may lack in variety ...

Trout Run Trail

IA - 11 miles

Trout Run Trail forms an 11-mile loop around Decorah, providing access to many of the area's natural treasures and views of beautiful Iowa countryside. Although there are many places to hop on the trail, ...

Wapsi-Great Western Line Trail

IA - 18.5 miles

The 18.5 mile long Wapsi-Great Western Line Trail follows the abandoned Chicago Great Western Railway grade between Riceville and the Iowa/Minnesota State Line. The corridor was originally built by the ...

Winnebago Trail

IA - 2 miles

Mason City's Winnebago Trail connects MacNider Campground, East Park, residential neighborhoods and the city's municipal swimming pool with the Lime Creek Nature Center just outside city limits. Along ...

Blazing Star State Trail

MN - 6 miles

The Blazing Star State Trail is located in Albert Lea, near Minnesota’s southern border. The town is known as “The Land Between the Lakes,” and the trail begins on the northern shore of one of the state’s ...

Charley Western Recreational Trailway

IA - 4 miles

The Charley Western Recreational Trailway provides a useful off-road route around the outer limits of Charles City. Built on the site of the former Charles City Western Railway, the trail runs along 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 ...

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 Great ...

Accordion

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 agricultural ...

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 ...

Harry Cook Nature Trail

IA - 2 miles

The Harry Cook Nature Trail runs for 2 miles from the edge of the small city of Osage, Iowa to the city's public Spring Park. The trail, which opened in the early 1990s, occupies the bed of an abandoned ...

NIACC Trail

IA - 2.2 miles

The NIACC Trail in Cerro Gordo County, Iowa, connects the campus of North Iowa Area Community College with the edge of downtown Mason City. The trail provides a convenient and safe alternative to biking ...

Prairie Farmer Recreational Trail

IA - 20 miles

The Prairie Farmer Rec. Trail (a.k.a. Winneshiek County Trail) was named for a radio show once broadcast throughout the Midwest. The trail occupies the right-of-way of the former Milwaukee Railroad, which ...

Riverside Trail (IA)

IA - 1.2 miles

Charles City's Riverside Trail runs for a little over a mile along the banks of the Cedar River, providing gorgeous views and recreational opportunities, as well as access to several city parks. Starting ...

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 Houston. ...

Shooting Star State Trail

MN - 18.8 miles

Shooting Star State Trail, currently 19 miles long, is an 8-foot-wide asphalt path from LeRoy (east) to Rose Creek (west). It follows an unused railroad bed on Milwaukee Road, which once stretched from ...

Trolley Trail (Clear Lake/Mason City)

IA - 6.2 miles

Most of northern Iowa's Trolley Trail is a straight line paralleling both 255th St./4th Ave. and the operational trolley tracks on the other side of the road. But what the Trolley Trail may lack in variety ...

Trout Run Trail

IA - 11 miles

Trout Run Trail forms an 11-mile loop around Decorah, providing access to many of the area's natural treasures and views of beautiful Iowa countryside. Although there are many places to hop on the trail, ...

Wapsi-Great Western Line Trail

IA - 18.5 miles

The 18.5 mile long Wapsi-Great Western Line Trail follows the abandoned Chicago Great Western Railway grade between Riceville and the Iowa/Minnesota State Line. The corridor was originally built by the ...

Winnebago Trail

IA - 2 miles

Mason City's Winnebago Trail connects MacNider Campground, East Park, residential neighborhoods and the city's municipal swimming pool with the Lime Creek Nature Center just outside city limits. Along ...

Recent Trail Reviews

Root River State Trail

Might be biased..

September, 2016 by ruthef

We live in the Preston area and moved here due to my husband's love of flyfishing. The Root River trail runs along the Root, but also along Camp Creek by Preston. It's lovely to walk or bike these trails, but those of you who like to fish can find some fairly good access to the streams as well!

Root River State Trail

Trail closed between Peterson and Rushford

August, 2016 by fluegel.becky

Scheduled closure until 9/2/16to repair/resurface.much needed repairs will make this trail awesome!

Root River State Trail

August, 2016 by fluegel.becky

Rode this trail 7/16. Beautifully smooth and scenic from Preston to Peterson. Rough trail to Rushford. Had a great burger at Shawnee's in Rushford. Nice bike stop in Lanesboro with bathrooms, water,air-this area is busier during the weekend so expect a bit more company in this area. There are several legs in this trail, all well marked. Just an exceptional trail.

Accordion

Trout Run Trail

very nice trail

July, 2016 by tnsa1

I highly recommend this trail; it is one of the nicest that I have rode. The views are wonderful, and there are plenty of places to stop and take it all in. Yes there are hills, but the climbs are worth the effort. If you are in the area this one is a must do!

Wapsi-Great Western Line Trail

Area secret - nice trail

July, 2016 by jlvcats

Trail was more interesting than I was expecting. Seems like it's location probably keeps it a bit of a secret. I would definitely ride it again. Some more details below:
It had changing scenery including rural (fields doing well in July, Amish family farming, horses with foals), wooded areas (some tunnel-like with trees), deer crossed the path, many birds and other wildlife, long boardwalk/deck trail through wetland, all with mostly level grade with some curves and short hills for some variety. Several miles were actually concrete instead of asphalt (I've never encountered that on a public trail before).
Had the trail mostly to ourselves on a holiday. It is in great condition except for just a few minor spots that were marked.
Only "neutral" comments are that we started in Riceville at the trailhead, but the parking lot only contained 1 non-HC spot. However the street was bare so we simply parked on it. Don't know if it ever gets so busy where that would be a problem.
Signage is better than many trails, but couple times needed to look around a bit more to find which direction the trail continued (when crossing some gravel roads), had to shortly go onto some rural (low travel) roads for a bit, and then there is the one short section that requires riding on a country gravel road to "portage" to the trail. This gap was somewhere around 11 miles north of Riceville, so you could skip that and get a nice 22 mile round trip in witout it.

Shooting Star State Trail

Pleasant ride, couple of bumps

July, 2016 by krbailleucpa

This is a pleasant enough trail. Most of it runs along beside a highway, but in many places there are trees and bushes shielding you from the road. The trail is asphalt, but there are several places where there are big bumps, as if the asphalt was put down in sections, with small breaks between each section. Many of the bumps have been marked with red paint, but the paint has faded and the bumps are still difficult to steer around.
The eastern end, approaching Le Roy, moves away from the highway and winds around a state park. It's quite pretty and very secluded and shady.

Trout Run Trail

Nice, but oh, those hills!

July, 2016 by krbailleucpa

The Trout Run Trail is actually a big loop around the town of Decorah. The east and north sides are mostly flat, as it winds around the edge of town. But the west and south sides are nothing but up and down and up again. Many hills are switchbacks, so even when you get a downhill, you have to apply the brakes and carefully steer around sharp curves, so you don't even get to coast for as long as you'd like.
Despite the excruciating hills, it is an attractive well-maintained trail, with scenery ranging from residential to industrial to riverside bluffs to open farmers' fields.

Root River State Trail

Root River Trail - Houston to Fountain to Houston

October, 2015 by javb76

A buddy and I rode this trail last weekend round trip starting out at Houston with the turnaround at Fountain. I was impressed with the overall quality of the surface, signage along the way and the scenery. This area of Minnesota is surprising hilly and the last 7 miles into Fountain was a tough climb (guessing a 600ft climb) with about 35 miles already peddled. After some food and beverage at the bent wrench bar/restuarant in Fountain we turned around and heading back down the to Lanesboro. I was surpised at the how steep the climb up to Fountian really was. this trail is an absolute gem with its varied topography and near pristine trail condition. It was well worth the drive from chicago. Highly recommend this trail. One of the most enjoyable trails I've ridden.

Trolley Trail (Clear Lake/Mason City)

Mason City to Clear Lake

October, 2015 by tammy.crookshank

Took the trail from Newman High School to Clear Lake and back. The trail condition is good. The trail runs along a busy highway. It is relatively flat and an easy ride. The trail does continue around the lake but much of it is on the road around Clear Lake that is marked ""shared road" but does not have a dedicated bike lane. Lots of bike friendly signs but no safety markings on the road. Lake view is often blocked by houses. Streets are busy.

Harmony-Preston Valley State Trail

Worth the long drive.

October, 2015 by gutwrencher

While I enjoyed the Root River trail from Lanesboro tut o Houston and back, It was anticlimactic or me. Yes....we were forced to miss the peak fall colors, but it was sunny but windy and cool....around 57. The best discovery was actually the Pedal Pushers Cafe in Lanesboro. The next day it was colder with highs flexing between 46 and 52....and NO sun. Despite this, it was the best ride of the weekend. LOVE this trail. Fun hills, good veiws, very few cyclists between Preston and Harmony. Estellas in Harmony....some of the best food anywhere on texting trail system. Drove up from Iowa City and will return.

Root River State Trail

Absolutely Fabulous!

September, 2015 by kempro

Made a special trip just to ride this trail after research and reading reviews. We were not disappointed in the least. We dropped a vehicle in Whalan and rode from Fountain east approximately 16.5 easy miles. This was the best part of our plan as the first 5 miles were downhill! We literally had to lightly pedal only twice over that span. The scenery couldn't be more beautiful. Rolling farmland, forest, and bluffs add to the frequent river views. The trail is extremely well maintained with picnic benches every mile and log shelters. The bicycle epicenter was in the quaint, lovely town of Lanesboro. Plenty of shops, cafes, and bars to satisfy every taste. Strangely though, this town seems to have a "fly issue". The stockyards are just two blocks from the center of town, so there seems to be an overabundance of flies in every place we stopped. I wonder if it was the time of year, or a constant irritation. Regardless, we thoroughly enjoyed this trip and plan to return next year.
Attention Road Bikers...Highway 16 from La Crescent west offers little traffic, wide shoulders, smooth pavement, and lovely rolling terrain!

Root River State Trail

A Gem Of A Trail

September, 2015 by heochief

We rode this trail from Houston to Fountain including the spur that goes from Lanesboro to Pearson. The trail was incredible as it follows the Root River for a majority. The scenic bluffs, rock cuts, Farming country and corn fields along the river were the driving force for us to complete our century ride that day. The trail passes through many towns that offer food, beverages and historic old buildings. All though the trail is scenic through out we were partial to the portion between Houston and Rushford. The bridges were long over the Root River and offered great views of the bluffs from the bridges. The trail does have a couple of challenges though. The trail is 100% paved asphalt and is in good condition between Houston and Petersen and great condition from Petersen to Fountain. The trail does seem to go uphill going west from Houston to Fountain. Even though railroad grade with a west headwind it took additional time. There is a challenging hill about 4 miles west of Houston going west and a even more challenging hill just east of Fountain. That was a steep five mile incline. All though manageable it was a accomplishment for us to climb that beast. We had a quick lunch and a couple of beers at a bar and grill in fountain. Then it was the return trip to round us out at 101.18 miles for the day. This trail was a gem and is highly recommended.

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