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Crestwood Trails and Maps

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Looking for the best trails around Crestwood?

Find the top rated trails in Crestwood, 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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81 Results
Activities
Length
Surfaces
Type

Bloomingdale Trail (The 606)
2.7 mi
State: IL
Asphalt, Concrete

Buffalo Creek Trail
3.2 mi
State: IL
Crushed Stone

Burnham Greenway
5.3 mi
State: IL
Asphalt

Busse Woods Trail
11.2 mi
State: IL
Asphalt

Cal-Sag Trail
13.8 mi
State: IL
Asphalt

Calumet Trail
9.1 mi
State: IN
Crushed Stone

Centennial Trail (IL)
13 mi
State: IL
Asphalt

Chesapeake and Ohio Greenway
1.9 mi
State: IN
Asphalt

Chicago Lakefront Trail
19 mi
State: IL
Asphalt, Concrete

Commonwealth Edison Bikeway
1.5 mi
State: IL
Asphalt

Danada and Herrick Lake Regional Trail
5.8 mi
State: IL
Crushed Stone

Deer Grove Trail
3.9 mi
State: IL
Asphalt

Des Plaines River Trail
56.2 mi
State: IL
Asphalt, Crushed Stone, Dirt, Gravel

DuPage River Trail
29.5 mi
State: IL
Asphalt

Dunes Kankakee Trail
3.2 mi
State: IN
Asphalt

East Northbrook Trail
1.1 mi
State: IL
Asphalt

El Paseo
0.1 mi
State: IL
Asphalt

Erie Lackawanna Trail
17.7 mi
State: IN
Asphalt

Fermilab Trail
5.8 mi
State: IL
Asphalt, Concrete

Fox River Trail (IL)
44.6 mi
State: IL
Asphalt, Concrete, Crushed Stone
Accordion

Great Western Trail (DuPage County)
12 mi
State: IL
Crushed Stone

Great Western Trail (IL)
17 mi
State: IL
Asphalt, Crushed Stone

Green Bay Trail
8.9 mi
State: IL
Asphalt, Concrete, Crushed Stone

Grove Road Trail
3 mi
State: IL
Asphalt

Hickory Creek Bikeway
3.7 mi
State: IL
Asphalt

Illinois & Michigan Canal State Trail
79.5 mi
State: IL
Asphalt, Crushed Stone, Grass, Gravel

Illinois Prairie Path
58.4 mi
State: IL
Asphalt, Concrete, Crushed Stone

Iron Horse Heritage Trail
2.4 mi
State: IN
Asphalt

John Husar I&M Canal Trail
8.9 mi
State: IL
Asphalt

Joliet Junction Trail
4.3 mi
State: IL
Asphalt

Kankakee River Trail
10.6 mi
State: IL
Asphalt, Crushed Stone

Lake George Trail
3.1 mi
State: IN
Asphalt

Lincolnwood Valley Line Trail
1.3 mi
State: IL
Asphalt

Little Calumet River Levee Trail

6 mi
State: IN
Asphalt

Major Taylor Trail
7.5 mi
State: IL
Asphalt

Marquette Trail
2.1 mi
State: IN
Crushed Stone

Middlefork Savanna Trail

4.3 mi
State: IL
Crushed Stone, Gravel

Millennium Trail
30.7 mi
State: IL
Asphalt, Concrete, Crushed Stone

Monon Trail (Lake County)
4.4 mi
State: IN
Asphalt

North Branch Riverwalk
0.6 mi
State: IL
Asphalt

North Branch Trail
21.3 mi
State: IL
Asphalt

North Shore Bike Path
7.7 mi
State: IL
Asphalt, Crushed Stone

North Shore Channel Trail
6.7 mi
State: IL
Asphalt, Concrete, Dirt

Northerly Island Trail
1 mi
State: IL
Asphalt, Concrete

Oak Savannah Trail
9.5 mi
State: IN
Asphalt

Old Plank Road Trail
21.7 mi
State: IL
Asphalt

Orland Park Bikeway
6.7 mi
State: IL
Asphalt, Concrete

Oswego Prairie Trail
0.5 mi
State: IL
Asphalt

Palatine Trail
9.6 mi
State: IL
Asphalt, Concrete

Palos Heights Bike Trail
2 mi
State: IL
Asphalt

Paul Douglas and Crabtree Preserve Trail System
9.2 mi
State: IL
Asphalt

Pennsy Greenway
7.9 mi
State: IL, IN
Asphalt

Phyllis Harmon Path
1.1 mi
State: IL
Asphalt

Poplar Creek Trail
9.5 mi
State: IL
Asphalt

Prairie Duneland Trail
10.3 mi
State: IN
Asphalt

Prairie Point Trail
2 mi
State: IL
Asphalt

Prairie Trail (IL)
26.5 mi
State: IL
Asphalt, Crushed Stone, Dirt, Gravel

Prospect Heights Bike Path
4.2 mi
State: IL
Asphalt

Randall Road Bike Trail
3.9 mi
State: IL
Asphalt

River Bend Trail (Silver Glen Trail)
4.4 mi
State: IL
Asphalt

Robert McClory Bike Path
25.4 mi
State: IL
Asphalt, Concrete, Crushed Stone

Rock Run Greenway Trail
12.3 mi
State: IL
Asphalt, Concrete, Crushed Stone

Salt Creek Trail (IL)
26.7 mi
State: IL
Asphalt, Cinder, Woodchips

Skokie Valley Trail (Cook County)
2 mi
State: IL
Asphalt

Skokie Valley Trail (Lake County)
9.8 mi
State: IL
Asphalt

Southern Dupage County Regional Trail
46 mi
State: IL
Asphalt, Crushed Stone

Tall Grass Greenway Trail
3.83 mi
State: IL
Asphalt

Techny Trail
3 mi
State: IL
Asphalt, Concrete

Thorn Creek Trail
17.2 mi
State: IL
Asphalt

Timber Ridge Trail
1 mi
State: IL
Gravel

Tinley Creek Trail (North)
24 mi
State: IL
Asphalt

Tinley Creek Trail (South)
3.6 mi
State: IL
Asphalt

Turkey Creek Trail
0.8 mi
State: IN
Asphalt

Union Pacific Recreation Path
1 mi
State: IL
Asphalt

Valley Line Trail
1.1 mi
State: IL
Asphalt

Veterans Memorial Bikeway (IN)
8.3 mi
State: IN
Asphalt, Dirt, Gravel

Veterans Memorial Trail
1.5 mi
State: IL
Asphalt

Virgil L. Gilman Trail
11.4 mi
State: IL
Asphalt

Waterfall Glen
9.5 mi
State: IL
Crushed Stone, Grass

Waubonsie Trail
3.2 mi
State: IL
Asphalt

Wauponsee Glacial Trail
22.3 mi
State: IL
Asphalt, Crushed Stone
Trail Image Trail Name States Length Surface Rating
The Bloomingdale Trail, part of “The 606” park system, is a 3-mile, elevated rail-trail on Chicago’s northwest side. Built on a former rail line, the trail sits 17 feet above four of the city’s...
 IL 2.7 mi Asphalt, Concrete
The Buffalo Creek Trail makes a loop around the scenic Buffalo Creek Forest Preserve in Long Grove. The crushed-gravel trail provides access to facilities throughout the park. Along the way, you’ll...
 IL 3.2 mi Crushed Stone
The Burnham Greenway is composed of two distinct portions that both run along a former railroad corridor between Chicago and Lansing, Illinois. There are plans to extend and connect these short...
 IL 5.3 mi Asphalt
The Busse Woods Trail system is located within Ned Brown Forest Preserve, a 3,700-acre property in the northwestern suburbs of Chicago. There are 11.2 miles of paved trails for cyclists, equestrians...
 IL 11.2 mi Asphalt
The Cal-Sag Trail (or, Calumet-Sag Trail) is currently under active construction. As of early 2018, it has a competed section of about 13 miles, stretching from near its western terminus at the John...
 IL 13.8 mi Asphalt
The Calumet Trail traverses the south side of the Indiana Dunes National Lakeshore, a unique ecosystem of forest, marsh, dunes and beach along Lake Michigan. This dirt and crushed limestone path...
 IN 9.1 mi Crushed Stone
Illinois’ Centennial Trail runs through parts of three suburban counties from Willow Springs Road to Romeo Road/135th Street southwest of Chicago. The trail occupies a thin strip of land between the...
 IL 13 mi Asphalt
The Chesapeake and Ohio Greenway (also referred to as the C&O Trail) offers a short, paved route through Merrillville, a town just a few miles south of Gary and the southern tip of Lake Michigan. The...
 IN 1.9 mi Asphalt
The Chicago Lakefront Trail is aptly named; it spans 19 miles along the shore of Lake Michigan, going right through downtown Chicago and passing many cultural and tourist attractions throughout the...
 IL 19 mi Asphalt, Concrete
The Commonwealth Edison Bikeway is a short paved trail that occupies an overhead electric utility corridor owned by Commonwealth Edison, the local utility company—hence the trail's name. While lacking...
 IL 1.5 mi Asphalt
This regional trail connects two of DuPage County's forest preserves—Herrick Lake and Danada—on a crushed stone pathway nearly 6 miles long. Together, the preserves cover more than 1,600 acres of...
 IL 5.8 mi Crushed Stone
The Deer Grove Trail is one of several great Chicagoland trails located in properties of the Forest Preserve of Cook County. Deer Grove is the oldest of all the Cook County preserves. It's comprised...
 IL 3.9 mi Asphalt
The Des Plaines River Trail runs alongside the Des Plaines River for just over 56 miles, protecting watershed habitat and forestland through much of Lake and Cook Counties. The trail is a natural...
 IL 56.2 mi Asphalt, Crushed Stone, Dirt, Gravel
The DuPage River Trail spans nearly 30 miles across two counties: DuPage and Will. It's currently open in several disconnected segments mainly in parks and forest preserves beginning in Warrenville...
 IL 29.5 mi Asphalt
The Dunes Kankakee Trail is a 3-mile walking and bike path that begins in the Indiana Dunes State Park and travels south to Chesterton. It connects the Calumet Trail, which is also in the state park,...
 IN 3.2 mi Asphalt
The East Northbrook Trail is a 1-mile route through a wooded corridor adjacent to an out-of-service rail corridor in the Village of Northbrook. The trail provides access to residential neighborhoods,...
 IL 1.1 mi Asphalt
El Paseo runs through the vibrant Chicago neighborhood of Pilsen, once home to a large Czech population but now the center of the Lower West Side’s Latino community. The neighborhood is filled with...
 IL 0.1 mi Asphalt
The Erie Lackawanna Trail rolls nearly 18 miles between Crown Point and Hammond, two former rail junctions whose early fortunes were tied to the tracks carrying people and goods to and from Chicago....
 IN 17.7 mi Asphalt
The Fermilab Trail garners its name by running though the campus of the Fermi National Accelerator Laboratory (Fermilab), the former home of the Tevatron particle accelerator. The 3.9-mile particle...
 IL 5.8 mi Asphalt, Concrete
The the Fox River Trail (FRT) was built on stretches of three former railroads: Chicago, Aurora & Elgin;  Aurora, Elgin, & Fox River Electric; and Chicago & North Western. Today, it hosts a multitude...
 IL 44.6 mi Asphalt, Concrete, Crushed Stone
Accordion
The eastern segment of the Great Western Trail in Illinois follows 12 miles of an abandoned railway corridor through DuPage County, between Villa Park and West Chicago. There are plans to extend the...
 IL 12 mi Crushed Stone
The western segment of the Great Western Trail in Illinois follows 17 miles of a former railway corridor through DeKalb and Kane counties, between LeRoy Oakes Forest Preserve and the town of Sycamore....
 IL 17 mi Asphalt, Crushed Stone
The 9-mile Green Bay Trail runs parallel to Chicago's Metra commuter rail line north of the Chicago city limits. Stretching through North Shore towns such as Kenilworth, Winnetka, Highland Park and...
 IL 8.9 mi Asphalt, Concrete, Crushed Stone
The Grove Road Trail parallels the local thoroughfare in the Village of Oswego, located near the southwestern edge of the Chicagoland metropolitan area. In the north, the trail begins on the east...
 IL 3 mi Asphalt
The Hickory Creek Bikeway offers nearly 4 miles of paved pathway through a wooded preserve. On its western end, the trail begins at Hickory Creek Barrens Nature Preserve and Lincolnway Road; on the...
 IL 3.7 mi Asphalt
The Illinois and Michigan Canal State Trail follows the eponymous waterway alongside the Illinois River. The trail runs along the old canal towpath from LaSalle to the historical quarry town of...
 IL 79.5 mi Asphalt, Crushed Stone, Grass, Gravel
The Illinois Prairie Path (IPP) was one of the nation’s first rail-trail conversions. It consists of five connected trail segments with three main branches that converge at Volunteer Park (West...
 IL 58.4 mi Asphalt, Concrete, Crushed Stone
The Iron Horse Heritage Trail in Portage, Indiana, runs for over 2 miles between Max Mochal Road (SR 149) at the east end and Hamstrom Rd. at the west end. The trail passes through a greenway corridor...
 IN 2.4 mi Asphalt
The John Husar I&M Canal Trail is the northernmost trail developed on the Illinois & Michigan Canal National Heritage Corridor. The Illinois & Michigan Canal provided the final link in the water route...
 IL 8.9 mi Asphalt
The Joliet Junction Trail is a paved path that travels north–south through the west side of Joliet. It occupies an abandoned Elgin, Joliet and Eastern Railway corridor that in its last years was known...
 IL 4.3 mi Asphalt
The Kankakee River Trail is fairly wooded and runs primarily through Kankakee River State Park. Walkers, bicyclists, and cross-country skiers can enjoy more than ten miles of trail along the north...
 IL 10.6 mi Asphalt, Crushed Stone
As the name suggests, the Lake George trail travels along the north shore of Lake George, turning north at Calumet Ave/US 41 to skirt the east shore of Wolf Lake. From Lake George the trail also heads...
 IN 3.1 mi Asphalt
The Lincolnwood Valley Line Trail connects the existing Valley Line Trail (Sauganash Trail) to the Skokie Valley Trail in Cook County.  Like the previous segments, this trail occupies a former Union...
 IL 1.3 mi Asphalt
Little Calumet River Levee Trail stretches from Munster to Gary, Indiana. The trail zigs and zags through a number of local parks including Riverside Park, Wicker Memorial Park, Homestead Park,...
 IN 6 mi Asphalt
The Major Taylor Trail is named after legendary African American cyclist Marshall “Major” Taylor, who was one of the most celebrated bicycle racers of the late nineteenth century, setting several...
 IL 7.5 mi Asphalt
The Marquette Trail offers picturesque views of Lake Michigan as it travels through the Indiana Dunes National Lakeshore. This scenic route follows an abandoned rail line through a variety of diverse...
 IN 2.1 mi Crushed Stone
The Middlefork Savanna Forest Preserve is a natural gem hidden in an high-income neighborhood of Lake Forest, Illinois.  Those 600 acres are home to perhaps the best-preserved example of the rare...
 IL 4.3 mi Crushed Stone, Gravel
The Millennium Trail currently spans just over 30 miles in two disconnected segments, but there are plans to extend it to 35 miles and connect it to the Des Plaines River Trail. The trail goes through...
 IL 30.7 mi Asphalt, Concrete, Crushed Stone
The Monon Trail in Lake County, Indiana—not to be confused with the trail of the same name in Indianapolis—links the two Chicago suburbs of Hammond and Munster. The paved trail occupies an abandoned...
 IN 4.4 mi Asphalt
The North Branch Riverwalk is a 0.6 mile biking and walking trail located on Chicago's northside along the North Branch of the Chicago River, nestled between Gordon Tech High School and Lane Tech High...
 IL 0.6 mi Asphalt
The North Branch Trail follows the North Branch of the Chicago River over 20 miles through Cook County. The trail was originally a dirt path often used for horseback riding; though it’s now paved, an...
 IL 21.3 mi Asphalt
The North Shore Bike Path runs for nearly 8 miles between Lake Bluff and Mundelein, paralleling State Route 176 for the path's entire length. The trail is one of dozens in the Chicagoland area, all of...
 IL 7.7 mi Asphalt, Crushed Stone
The North Shore Channel Trail extends from the junction of Green Bay Road and McCormick Boulevard in northern Evanston to the junction of Lawrence Avenue and Francisco Avenue in Chicago. All but the...
 IL 6.7 mi Asphalt, Concrete, Dirt
The Northerly Island Trail offers access to a vast, natural oasis in one of the largest cities in America. Chicago’s Northerly Island—actually a 91-acre peninsula—was designed by Daniel H. Burnham,...
 IL 1 mi Asphalt, Concrete
First-time visitors to the Oak Savannah Trail might be surprised at the profusion of natural areas they’ll encounter as they travel the 8 miles between Hobart and Griffith in northern Indiana’s...
 IN 9.5 mi Asphalt
The Old Plank Road Trail travels nearly 22 miles between Chicago Heights and Joliet across a densely populated suburban landscape, where you’re never far from a café or espresso stand. Still, you...
 IL 21.7 mi Asphalt
The Orland Park Bikeway provides a great connector across the Chicago suburb of Orland Park. On its southern end, the trail begins at W. 159th Street and winds its way through Centennial Park, which...
 IL 6.7 mi Asphalt, Concrete
The Oswego Prairie Trail is a short paved route that occupies an overhead electric utility corridor owned by Commonwealth Edison. The path forms a direct link between two parks in Oswego—Farmington...
 IL 0.5 mi Asphalt
The village of Palatine has connected many of its community assets with two long sections of off-road, multi-use trail. The more popular northern section is the one most references call simply and...
 IL 9.6 mi Asphalt, Concrete
The Palos Heights Bike Trail offers a north-south route through residential and commercial areas on the west side of the community. It's also a key connector between two regionally important...
 IL 2 mi Asphalt
The Paul Douglas and Crabtree Preserve Trail System connects two large nature preserves in northwestern Cook County. The trail begins at the Old Stover Trailhead in the Crabtree Preserve, near the...
 IL 9.2 mi Asphalt
The Pennsy Greenway is currently open in three segments between Calumet City, Illinois, and Schererville, Indiana. The northern portion begins at the southern end of the Burnham Greenway in Calumet...
 IL, IN 7.9 mi Asphalt
Although the Phyllis Harmon Path is short, it's an important connector in an east-west bike/ped route between Arlington Heights and Glencoe. Following Dundee Road, the paved trail goes from the Des...
 IL 1.1 mi Asphalt
The Poplar Creek Trail is a 9.5-mile paved loop around Poplar Creek Forest Preserve near Hoffman Estates. The trail has a couple of hills but is otherwise level and makes for a pleasant journey...
 IL 9.5 mi Asphalt
Prairies and dunes are just two of the natural features you’ll experience on the Prairie Duneland Trail, located just a few miles south of the Lake Michigan shoreline and the Indiana Dunes National...
 IN 10.3 mi Asphalt
The Prairie Point Trail is a scenic neighborhood route that connects twice to the longer Grove Road Trail. While never far from houses, the trail offers surprising scenery, including a stretch along a...
 IL 2 mi Asphalt
The Prairie Trail runs the length of McHenry County and is managed by the McHenry County Conservation District. The rail-trail spans just over 26 miles from the Wisconsin border and the farms and...
 IL 26.5 mi Asphalt, Crushed Stone, Dirt, Gravel
Prospect Heights Bike Path runs between Woodland Trails Park and Country Garden Park, paralleling the commuter rail tracks on its north–south leg. The trail provides a nice off-road route through the...
 IL 4.2 mi Asphalt
The Randall Road Bike Trail offers a 4-mile paved north-south route along its namesake roadway in a suburb west of Chicago. A highlight of the journey is the trail's passage through the LeRoy Oakes...
 IL 3.9 mi Asphalt
The 4.4-mile River Bend Trail is so named for the loop of Fox River along which it follows on its eastern end. It's here that you can connect to the scenic Fox River Trail to travel 43 miles along the...
 IL 4.4 mi Asphalt
The Robert McClory Bike Path runs the length of Lake County, knitting together a string of communities on the north shore of Chicago all the way to the Wisconsin border. In 1997, the trail was named...
 IL 25.4 mi Asphalt, Concrete, Crushed Stone
The popular Rock Run Greenway Trail is a balanced mix of natural areas and cityscapes that alternate over the length of the trail. The natural areas are frequented by recreational users. The...
 IL 12.3 mi Asphalt, Concrete, Crushed Stone
The Salt Creek Trail travels nearly 27 miles from the Brookfield Zoo to Busse Woods Forest Preserve. Along the way it connects several beautiful county forest preserves and other woodland...
 IL 26.7 mi Asphalt, Cinder, Woodchips
The Skokie Valley Trail in Cook County parallels active train tracks in the Village of Skokie, providing easy access to both the Oakton–Skokie and Dempster–Skokie stations on the CTA’s Yellow Line....
 IL 2 mi Asphalt
An excellent example of land use in greater Chicago, the entire Skokie Valley Trail corridor is a rail-with-trail, paralleled by double tracks that sit about 40 feet to the west of the trail surface....
 IL 9.8 mi Asphalt
The Southern Dupage County Regional Trail connects multiple of the larger forest preserves in Dupage county together. Starting near the intersection of 75th st and Ogden Ave in Aurora, the trail runs...
 IL 46 mi Asphalt, Crushed Stone
The Tall Grass Greenway Trail is a trail that runs along the right of way for ComEd powerlines. The trail goes mainly through neighborhoods in south Naperville, and meets up with the south branch of...
 IL 3.83 mi Asphalt
The Techny Trail links downtown Glenview, a charming village northwest of Chicago, with the Techny Basin, a scenic wetlands area adjacent to the West Fork of the Chicago River's North Branch....
 IL 3 mi Asphalt, Concrete
The Thorn Creek Trail offers a paved 17-mile route traversing woodlands abundant with wildlife through several communities on the southern outskirts of Chicago.  The trail travels from Brownwell Woods...
 IL 17.2 mi Asphalt
The Timber Ridge trail is located on the eastern side of the Timber Ridge Forest Preserve in west Chicago. The preserve offers several trails, fishing, picnicking, and is home to Kline Creek Farms,...
 IL 1 mi Gravel
The northern section of the Tinley Creek Trail is a series of color-coded connected loops and spurs that weave through several forest preserves in Cook County. The 24-mile trail system is paved,...
 IL 24 mi Asphalt
The Tinley Creek Trail is currently in two segments. This southern segment is within the South Green Belt Forest Preserve between Flossmor and Matteson, just west of I-57. The trail traverses wooded...
 IL 3.6 mi Asphalt
Turkey Creek Trail is a short but sweet walk or ride through the beautiful Ivan Gatlin Nature Preserve in the northwestern Indiana community of Schererville. This wetland area provides the opportunity...
 IN 0.8 mi Asphalt
The Union Pacific Recreation Path offers a short route through the Village of Lincolnwood's east side between Devon and Touhy avenues. Following the former Union Pacific Railroad, the rail-trail...
 IL 1 mi Asphalt
Just 1 mile long, the Valley Line Trail—also known as the Sauganash Trail—extends between Bryn Mawr Avenue and Devon Avenue in the Chicago neighborhood of Sauganash. Two bridges allow for safe...
 IL 1.1 mi Asphalt
The Veterans Memorial Bikeway begins in Hebron in northwestern Indiana’s Porter County. From there, it follows the diagonal route of the former Pennsylvania Railroad for just over 8 miles through Lake...
 IN 8.3 mi Asphalt, Dirt, Gravel
Although just shy of two miles, the Veterans Memorial Trail provides a wooded, paved trail experience for residents in the Chicago suburbs of Romeoville, Lemont, and Woodridge. Those seeking a longer...
 IL 1.5 mi Asphalt
The Virgil L. Gilman Trail travels from quiet forest and prairie lands to bustling neighborhoods in just 11 miles, linking a woodsy community college campus with the eastern Chicago suburb of...
 IL 11.4 mi Asphalt
The trail system in Waterfall Glen Forest Preserve makes a loop around the entire park. The preserve is geologically significant, featuring glacier-carved rock ridges, ravines and wetland potholes,...
 IL 9.5 mi Crushed Stone, Grass
The Waubonsie Trail links Boulder Hill and the Village of Oswego via a greenway corridor within a residential community. The eastern trailhead is in Jaycee Park, which offers a playground, picnic...
 IL 3.2 mi Asphalt
In just a few short miles, the Wauponsee Glacial Trail leaves the urban confines of Joliet to bask in open farmland and reclaimed tallgrass prairie where the bison roam again. Named for a glacial lake...
 IL 22.3 mi Asphalt, Crushed Stone

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Trails by activity

DuPage River Trail

IL - 29.5 miles

The DuPage River Trail spans nearly 30 miles across two counties: DuPage and Will. It's currently open in several disconnected segments mainly in parks and forest preserves beginning in Warrenville...

Virgil L. Gilman Trail

IL - 11.4 miles

The Virgil L. Gilman Trail travels from quiet forest and prairie lands to bustling neighborhoods in just 11 miles, linking a woodsy community college campus with the eastern Chicago suburb of...

Marquette Trail

IN - 2.1 miles

The Marquette Trail offers picturesque views of Lake Michigan as it travels through the Indiana Dunes National Lakeshore. This scenic route follows an abandoned rail line through a variety of diverse...

Middlefork Savanna Trail

IL - 4.3 miles

The Middlefork Savanna Forest Preserve is a natural gem hidden in an high-income neighborhood of Lake Forest, Illinois.  Those 600 acres are home to perhaps the best-preserved example of the rare...

Accordion

River Bend Trail (Silver Glen Trail)

IL - 4.4 miles

The 4.4-mile River Bend Trail is so named for the loop of Fox River along which it follows on its eastern end. It's here that you can connect to the scenic Fox River Trail to travel 43 miles along the...

Southern Dupage County Regional Trail

IL - 46 miles

The Southern Dupage County Regional Trail connects multiple of the larger forest preserves in Dupage county together. Starting near the intersection of 75th st and Ogden Ave in Aurora, the trail runs...

Thorn Creek Trail

IL - 17.2 miles

The Thorn Creek Trail offers a paved 17-mile route traversing woodlands abundant with wildlife through several communities on the southern outskirts of Chicago.  The trail travels from Brownwell Woods...

Des Plaines River Trail

IL - 56.2 miles

The Des Plaines River Trail runs alongside the Des Plaines River for just over 56 miles, protecting watershed habitat and forestland through much of Lake and Cook Counties. The trail is a natural...

Prairie Trail (IL)

IL - 26.5 miles

The Prairie Trail runs the length of McHenry County and is managed by the McHenry County Conservation District. The rail-trail spans just over 26 miles from the Wisconsin border and the farms and...

Great Western Trail (IL)

IL - 17 miles

The western segment of the Great Western Trail in Illinois follows 17 miles of a former railway corridor through DeKalb and Kane counties, between LeRoy Oakes Forest Preserve and the town of Sycamore....

Cal-Sag Trail

IL - 13.8 miles

The Cal-Sag Trail (or, Calumet-Sag Trail) is currently under active construction. As of early 2018, it has a competed section of about 13 miles, stretching from near its western terminus at the John...

Veterans Memorial Trail

IL - 1.5 miles

Although just shy of two miles, the Veterans Memorial Trail provides a wooded, paved trail experience for residents in the Chicago suburbs of Romeoville, Lemont, and Woodridge. Those seeking a longer...

Great Western Trail (DuPage County)

IL - 12 miles

The eastern segment of the Great Western Trail in Illinois follows 12 miles of an abandoned railway corridor through DuPage County, between Villa Park and West Chicago. There are plans to extend the...

Turkey Creek Trail

IN - 0.8 miles

Turkey Creek Trail is a short but sweet walk or ride through the beautiful Ivan Gatlin Nature Preserve in the northwestern Indiana community of Schererville. This wetland area provides the opportunity...

Palos Heights Bike Trail

IL - 2 miles

The Palos Heights Bike Trail offers a north-south route through residential and commercial areas on the west side of the community. It's also a key connector between two regionally important...

Kankakee River Trail

IL - 10.6 miles

The Kankakee River Trail is fairly wooded and runs primarily through Kankakee River State Park. Walkers, bicyclists, and cross-country skiers can enjoy more than ten miles of trail along the north...

Tinley Creek Trail (South)

IL - 3.6 miles

The Tinley Creek Trail is currently in two segments. This southern segment is within the South Green Belt Forest Preserve between Flossmor and Matteson, just west of I-57. The trail traverses wooded...

Skokie Valley Trail (Cook County)

IL - 2 miles

The Skokie Valley Trail in Cook County parallels active train tracks in the Village of Skokie, providing easy access to both the Oakton–Skokie and Dempster–Skokie stations on the CTA’s Yellow Line....

Timber Ridge Trail

IL - 1 miles

The Timber Ridge trail is located on the eastern side of the Timber Ridge Forest Preserve in west Chicago. The preserve offers several trails, fishing, picnicking, and is home to Kline Creek Farms,...

Union Pacific Recreation Path

IL - 1 miles

The Union Pacific Recreation Path offers a short route through the Village of Lincolnwood's east side between Devon and Touhy avenues. Following the former Union Pacific Railroad, the rail-trail...

More Crestwood bike trailsView Fewer Crestwood bike trails

Chicago Lakefront Trail

IL - 19 miles

The Chicago Lakefront Trail is aptly named; it spans 19 miles along the shore of Lake Michigan, going right through downtown Chicago and passing many cultural and tourist attractions throughout the...

Pennsy Greenway

IL,IN - 7.9 miles

The Pennsy Greenway is currently open in three segments between Calumet City, Illinois, and Schererville, Indiana. The northern portion begins at the southern end of the Burnham Greenway in Calumet...

Busse Woods Trail

IL - 11.2 miles

The Busse Woods Trail system is located within Ned Brown Forest Preserve, a 3,700-acre property in the northwestern suburbs of Chicago. There are 11.2 miles of paved trails for cyclists, equestrians...

Veterans Memorial Bikeway (IN)

IN - 8.3 miles

The Veterans Memorial Bikeway begins in Hebron in northwestern Indiana’s Porter County. From there, it follows the diagonal route of the former Pennsylvania Railroad for just over 8 miles through Lake...

Accordion

Middlefork Savanna Trail

IL - 4.3 miles

The Middlefork Savanna Forest Preserve is a natural gem hidden in an high-income neighborhood of Lake Forest, Illinois.  Those 600 acres are home to perhaps the best-preserved example of the rare...

Deer Grove Trail

IL - 3.9 miles

The Deer Grove Trail is one of several great Chicagoland trails located in properties of the Forest Preserve of Cook County. Deer Grove is the oldest of all the Cook County preserves. It's comprised...

Waubonsie Trail

IL - 3.2 miles

The Waubonsie Trail links Boulder Hill and the Village of Oswego via a greenway corridor within a residential community. The eastern trailhead is in Jaycee Park, which offers a playground, picnic...

Palos Heights Bike Trail

IL - 2 miles

The Palos Heights Bike Trail offers a north-south route through residential and commercial areas on the west side of the community. It's also a key connector between two regionally important...

Wauponsee Glacial Trail

IL - 22.3 miles

In just a few short miles, the Wauponsee Glacial Trail leaves the urban confines of Joliet to bask in open farmland and reclaimed tallgrass prairie where the bison roam again. Named for a glacial lake...

Grove Road Trail

IL - 3 miles

The Grove Road Trail parallels the local thoroughfare in the Village of Oswego, located near the southwestern edge of the Chicagoland metropolitan area. In the north, the trail begins on the east...

Fox River Trail (IL)

IL - 44.6 miles

The the Fox River Trail (FRT) was built on stretches of three former railroads: Chicago, Aurora & Elgin;  Aurora, Elgin, & Fox River Electric; and Chicago & North Western. Today, it hosts a multitude...

Palatine Trail

IL - 9.6 miles

The village of Palatine has connected many of its community assets with two long sections of off-road, multi-use trail. The more popular northern section is the one most references call simply and...

Illinois & Michigan Canal State Trail

IL - 79.5 miles

The Illinois and Michigan Canal State Trail follows the eponymous waterway alongside the Illinois River. The trail runs along the old canal towpath from LaSalle to the historical quarry town of...

Union Pacific Recreation Path

IL - 1 miles

The Union Pacific Recreation Path offers a short route through the Village of Lincolnwood's east side between Devon and Touhy avenues. Following the former Union Pacific Railroad, the rail-trail...

Hickory Creek Bikeway

IL - 3.7 miles

The Hickory Creek Bikeway offers nearly 4 miles of paved pathway through a wooded preserve. On its western end, the trail begins at Hickory Creek Barrens Nature Preserve and Lincolnway Road; on the...

Prairie Duneland Trail

IN - 10.3 miles

Prairies and dunes are just two of the natural features you’ll experience on the Prairie Duneland Trail, located just a few miles south of the Lake Michigan shoreline and the Indiana Dunes National...

Buffalo Creek Trail

IL - 3.2 miles

The Buffalo Creek Trail makes a loop around the scenic Buffalo Creek Forest Preserve in Long Grove. The crushed-gravel trail provides access to facilities throughout the park. Along the way, you’ll...

Thorn Creek Trail

IL - 17.2 miles

The Thorn Creek Trail offers a paved 17-mile route traversing woodlands abundant with wildlife through several communities on the southern outskirts of Chicago.  The trail travels from Brownwell Woods...

Prairie Trail (IL)

IL - 26.5 miles

The Prairie Trail runs the length of McHenry County and is managed by the McHenry County Conservation District. The rail-trail spans just over 26 miles from the Wisconsin border and the farms and...

Skokie Valley Trail (Cook County)

IL - 2 miles

The Skokie Valley Trail in Cook County parallels active train tracks in the Village of Skokie, providing easy access to both the Oakton–Skokie and Dempster–Skokie stations on the CTA’s Yellow Line....

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Illinois Prairie Path

IL - 58.4 miles

The Illinois Prairie Path (IPP) was one of the nation’s first rail-trail conversions. It consists of five connected trail segments with three main branches that converge at Volunteer Park (West...

Oak Savannah Trail

IN - 9.5 miles

First-time visitors to the Oak Savannah Trail might be surprised at the profusion of natural areas they’ll encounter as they travel the 8 miles between Hobart and Griffith in northern Indiana’s...

Bloomingdale Trail (The 606)

IL - 2.7 miles

The Bloomingdale Trail, part of “The 606” park system, is a 3-mile, elevated rail-trail on Chicago’s northwest side. Built on a former rail line, the trail sits 17 feet above four of the city’s...

Cal-Sag Trail

IL - 13.8 miles

The Cal-Sag Trail (or, Calumet-Sag Trail) is currently under active construction. As of early 2018, it has a competed section of about 13 miles, stretching from near its western terminus at the John...

Accordion

El Paseo

IL - 0.1 miles

El Paseo runs through the vibrant Chicago neighborhood of Pilsen, once home to a large Czech population but now the center of the Lower West Side’s Latino community. The neighborhood is filled with...

Monon Trail (Lake County)

IN - 4.4 miles

The Monon Trail in Lake County, Indiana—not to be confused with the trail of the same name in Indianapolis—links the two Chicago suburbs of Hammond and Munster. The paved trail occupies an abandoned...

Union Pacific Recreation Path

IL - 1 miles

The Union Pacific Recreation Path offers a short route through the Village of Lincolnwood's east side between Devon and Touhy avenues. Following the former Union Pacific Railroad, the rail-trail...

John Husar I&M Canal Trail

IL - 8.9 miles

The John Husar I&M Canal Trail is the northernmost trail developed on the Illinois & Michigan Canal National Heritage Corridor. The Illinois & Michigan Canal provided the final link in the water route...

Dunes Kankakee Trail

IN - 3.2 miles

The Dunes Kankakee Trail is a 3-mile walking and bike path that begins in the Indiana Dunes State Park and travels south to Chesterton. It connects the Calumet Trail, which is also in the state park,...

Centennial Trail (IL)

IL - 13 miles

Illinois’ Centennial Trail runs through parts of three suburban counties from Willow Springs Road to Romeo Road/135th Street southwest of Chicago. The trail occupies a thin strip of land between the...

Calumet Trail

IN - 9.1 miles

The Calumet Trail traverses the south side of the Indiana Dunes National Lakeshore, a unique ecosystem of forest, marsh, dunes and beach along Lake Michigan. This dirt and crushed limestone path...

Fermilab Trail

IL - 5.8 miles

The Fermilab Trail garners its name by running though the campus of the Fermi National Accelerator Laboratory (Fermilab), the former home of the Tevatron particle accelerator. The 3.9-mile particle...

Marquette Trail

IN - 2.1 miles

The Marquette Trail offers picturesque views of Lake Michigan as it travels through the Indiana Dunes National Lakeshore. This scenic route follows an abandoned rail line through a variety of diverse...

Paul Douglas and Crabtree Preserve Trail System

IL - 9.2 miles

The Paul Douglas and Crabtree Preserve Trail System connects two large nature preserves in northwestern Cook County. The trail begins at the Old Stover Trailhead in the Crabtree Preserve, near the...

Wauponsee Glacial Trail

IL - 22.3 miles

In just a few short miles, the Wauponsee Glacial Trail leaves the urban confines of Joliet to bask in open farmland and reclaimed tallgrass prairie where the bison roam again. Named for a glacial lake...

Hickory Creek Bikeway

IL - 3.7 miles

The Hickory Creek Bikeway offers nearly 4 miles of paved pathway through a wooded preserve. On its western end, the trail begins at Hickory Creek Barrens Nature Preserve and Lincolnway Road; on the...

Tinley Creek Trail (North)

IL - 24 miles

The northern section of the Tinley Creek Trail is a series of color-coded connected loops and spurs that weave through several forest preserves in Cook County. The 24-mile trail system is paved,...

Illinois & Michigan Canal State Trail

IL - 79.5 miles

The Illinois and Michigan Canal State Trail follows the eponymous waterway alongside the Illinois River. The trail runs along the old canal towpath from LaSalle to the historical quarry town of...

North Branch Trail

IL - 21.3 miles

The North Branch Trail follows the North Branch of the Chicago River over 20 miles through Cook County. The trail was originally a dirt path often used for horseback riding; though it’s now paved, an...

Prospect Heights Bike Path

IL - 4.2 miles

Prospect Heights Bike Path runs between Woodland Trails Park and Country Garden Park, paralleling the commuter rail tracks on its north–south leg. The trail provides a nice off-road route through the...

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Recent Trail Reviews

Centennial Trail (IL)

Access closer

June, 2018 by ampozdol

We love riding this trail. Since it does not go through a lot of Forest Preserves you do not see many pedestrians. We rode to the end point off of Willow Springs road 6/16/18 and the bridge to the start of the path was blocked with signs saying that the bridge was closed until October 2018. No warning signs up the week before.

read more …

Centennial Trail (IL)

Excellent trail but, FYI

June, 2018 by markecklund

FYI, the bridge you use to access the trail from Columbia Woods in Willow Springs was suddenly closed today, 6/16/16. The sign says bridge out 6/18 which would be Monday & would make more sense but they put concrete barriers across already anyway. You’ll have to access the trail elsewhere until they finish their bridge repairs.

read more …

Oak Savannah Trail

Parked trains block the Oak Savannah trail.

June, 2018 by 1diver

Twice in one week a parked train in between Colfax and Hendricks blocked the Oak Savannah trail near the Oak Ridge Prairie. It doesn’t even look like there’s an engine hooked up to it. Riding home from Chesterton is very fusterating when the trail is blocked. The triail from OakRidge Prarie to Chesterton is a beautiful ride but the parked trains make it useless.

read more …
Accordion

Skokie Valley Trail (Lake County)

Great ride!

June, 2018 by matt.patruno

Love the length of this. Usually do it in a little over an hour, and at just under 20 Miles this is a perfect ride to help you maintain and work on a faster pace when training for those much longer rides. Surface is good enough, not the best but not even close to being bad. Good straight aways, only a few roadway crossings on the entire path so you can maintain a good speed without having to stop or slow down.

read more …

North Shore Bike Path

Lots of Stops

June, 2018 by matt.patruno

Trail surface is good, way too many stops though for roadways, etc. Rode after a rainy day so maybe that added to the low rating. A lot more routes in the area with less stops though.

read more …

Waterfall Glen

Agree with other 5 star reviews

June, 2018 by chrishawry

For the most part, I agree with the five star reviews. It is a beautiful trail that takes you through forest, past a beautiful overlook, over bridges and has several bathroom/outhouses every 3-4 miles (located in the parking lots). I did not see horse poop as one review indicated and I was able to handle the 4-5 larger hills (I'm in my 60's so most bikers should handle them fine). The trail wasn't too busy (midweek) and you get the feeling that you are far from civilization because of the vast number of trees and open spaces. I took the advice from one reviewer and went counterclockwise around the circle. I really think that it had better runs in that direction. The only negative for me is that the trail takes you across a couple of busy roads and traffic didn't stop for bikers. My distance clocked in a 10 miles. Finally, this trail is excellent for really hot days because of all the shade. Enjoy!

read more …

Kankakee River Trail

Kankakee River Trail Ride

June, 2018 by michael.scruggs

This is a fun filled ride along the beautiful Kankakee river. The new walk or bicycle only bridge, crossing the river near Riverside Hospital is a real plus.

read more …

Chicago Lakefront Trail

Amazing views!

May, 2018 by lamborghiniman75

This trail was perfect. I took my rollerblades with me while on vacation and skated here. It was very cool. The architecture is amazing for admiring and along a beach with things going on in the lake made for great scenery in all directions. Even took an intermission to get my feet in the sand since the trail goes on the beach. I will definitely be back on this trail next time I'm in Chicago!

read more …

North Shore Channel Trail

start stop kills this and badly sign posted

May, 2018 by kenneth_j_mitchell

Won’t be riding this again on the road bike. Fumes from roads make this not so pleasant. Sculptures and play ground for kids are great but that’s about it. Got lost when it flips to other side of river. This route is for kids on bikes, not serious cyclists. Fun all the same with the kids for sure

read more …

North Branch Trail

Best trail by a mile

May, 2018 by kenneth_j_mitchell

Coming from the uk I was pessimistic about city cycling. After getting bored of the lake front trail and north Sheridan/Green Bay road repeats this trail is a god send. Love it. Perfect for road biking and quiet(midweek) will continue to look for other trails but this one will be hard to beat.

read more …

Illinois & Michigan Canal State Trail

Bumpy ride

May, 2018 by ryanalf

I rode Ottawa to LaSalle. Sections of the trail were very rough. Motorbike tracks, moguls and stream remnants made the trail dangerous. The history and the washed out bridge are awesome(see photo).

read more …

Erie Lackawanna Trail

A nice spring day

April, 2018 by ryanalf

Rode mid April, the trail is all asphalt. Parking in Crown Point was easy. Many busy streets to cross.

read more …
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