Chester Trails and Maps

69 Reviews

Looking for the best trails around Chester?

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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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

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

19.9 mi
State: IA
Asphalt, Crushed Stone

Winnebago Trail

3.7 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...
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...
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...
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...
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...
IA 2 mi Crushed Stone
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...
IA 2.2 mi Asphalt
The Prairie Farmer Recreational Trail follows part of the former Chicago, Milwaukee, St. Paul and Pacific Railroad corridor, which traces its origins as far back as 1866. Its history lives on in...
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...
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...
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...
MN 18.8 mi Asphalt
The best place to begin the Trolley Trail is in Mason City in Ray Rorick Skate Park, located adjacent to the 81-acre Lester Milligan Park, which has two fishing and swimming ponds, hiking and biking...
IA 7.5 mi Asphalt
The Trout Run Trail provides an experience unique to any other in Iowa, with a hilly landscape that reminds trail users of the meteorite that struck the area long ago. The trail actually loops all the...
IA 11 mi Asphalt, Concrete
The Wapsi–Great Western Line Trail is a 19.9-mile pathway that comprises two separate segments of the former Chicago Great Western Railroad. Along the combined route, the trail passes through a...
IA 19.9 mi Asphalt, Crushed Stone
The Winnebago Trail provides the residents of Mason City with a safe, off-road link to nature, winding 3.7 miles from East Park and through residential areas to the Lime Creek Nature Center as it...
IA 3.7 mi Crushed Stone

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Trails by activity

Trout Run Trail

IA - 11 miles

The Trout Run Trail provides an experience unique to any other in Iowa, with a hilly landscape that reminds trail users of the meteorite that struck the area long ago. The trail actually loops all the...

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...

Trolley Trail (Clear Lake/Mason City)

IA - 7.5 miles

The best place to begin the Trolley Trail is in Mason City in Ray Rorick Skate Park, located adjacent to the 81-acre Lester Milligan Park, which has two fishing and swimming ponds, hiking and biking...

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...

Accordion

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...

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...

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...

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...

Winnebago Trail

IA - 3.7 miles

The Winnebago Trail provides the residents of Mason City with a safe, off-road link to nature, winding 3.7 miles from East Park and through residential areas to the Lime Creek Nature Center as it...

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...

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...

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...

Prairie Farmer Recreational Trail

IA - 20 miles

The Prairie Farmer Recreational Trail follows part of the former Chicago, Milwaukee, St. Paul and Pacific Railroad corridor, which traces its origins as far back as 1866. Its history lives on in...

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...

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...

Wapsi-Great Western Line Trail

IA - 19.9 miles

The Wapsi–Great Western Line Trail is a 19.9-mile pathway that comprises two separate segments of the former Chicago Great Western Railroad. Along the combined route, the trail passes through a...

Wapsi-Great Western Line Trail

IA - 19.9 miles

The Wapsi–Great Western Line Trail is a 19.9-mile pathway that comprises two separate segments of the former Chicago Great Western Railroad. Along the combined route, the trail passes through a...

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...

Trout Run Trail

IA - 11 miles

The Trout Run Trail provides an experience unique to any other in Iowa, with a hilly landscape that reminds trail users of the meteorite that struck the area long ago. The trail actually loops all the...

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...

Accordion

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...

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...

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...

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...

Winnebago Trail

IA - 3.7 miles

The Winnebago Trail provides the residents of Mason City with a safe, off-road link to nature, winding 3.7 miles from East Park and through residential areas to the Lime Creek Nature Center as it...

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...

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...

Trolley Trail (Clear Lake/Mason City)

IA - 7.5 miles

The best place to begin the Trolley Trail is in Mason City in Ray Rorick Skate Park, located adjacent to the 81-acre Lester Milligan Park, which has two fishing and swimming ponds, hiking and biking...

Prairie Farmer Recreational Trail

IA - 20 miles

The Prairie Farmer Recreational Trail follows part of the former Chicago, Milwaukee, St. Paul and Pacific Railroad corridor, which traces its origins as far back as 1866. Its history lives on in...

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...

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...

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...

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...

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...

Prairie Farmer Recreational Trail

IA - 20 miles

The Prairie Farmer Recreational Trail follows part of the former Chicago, Milwaukee, St. Paul and Pacific Railroad corridor, which traces its origins as far back as 1866. Its history lives on in...

Accordion

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...

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...

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...

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...

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...

Trout Run Trail

IA - 11 miles

The Trout Run Trail provides an experience unique to any other in Iowa, with a hilly landscape that reminds trail users of the meteorite that struck the area long ago. The trail actually loops all the...

Wapsi-Great Western Line Trail

IA - 19.9 miles

The Wapsi–Great Western Line Trail is a 19.9-mile pathway that comprises two separate segments of the former Chicago Great Western Railroad. Along the combined route, the trail passes through a...

Trolley Trail (Clear Lake/Mason City)

IA - 7.5 miles

The best place to begin the Trolley Trail is in Mason City in Ray Rorick Skate Park, located adjacent to the 81-acre Lester Milligan Park, which has two fishing and swimming ponds, hiking and biking...

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...

Winnebago Trail

IA - 3.7 miles

The Winnebago Trail provides the residents of Mason City with a safe, off-road link to nature, winding 3.7 miles from East Park and through residential areas to the Lime Creek Nature Center as it...

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...

Recent Trail Reviews

Root River State Trail

Love this trail

August, 2017 by crosscountry79

Went from Rushford to Whalen and the trail was in great shape. It was the first time I was on a trail in Minnesota. Great first impression. Will try other half after Whalen and the harmony trail next.

Blazing Star State Trail

very nice trail

July, 2017 by louitlemert

new pavement beautiful scenery very nice ride I will return to explore side trails and surrounding areas

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!

Accordion

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.

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.

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