Explore the best rated trails in Winnetka, IL. Whether you're looking for an easy walking trail or a bike trail like the Illinois & Michigan Canal State Trail and Tall Grass Greenway Trail. With more than 113 trails covering 1087 miles you’re bound to find a perfect trail for you. Click on any trail below to find trail descriptions, trail maps, photos, and reviews.
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Running between the suburbs of Chicago Heights and Joliet, the Old Plank Road Trail offers views of oak trees and sugar maples, prairie grasses, and wildflowers that peek up through the...
The KR Trail is a new addition to Kenosha County’s growing bike-ped network. The trail picks up where the Kenosha County Bike Trail leaves off, in Petrifying Springs Park. From the northwest corner of...
The Kenosha County Bike Trail is open in two sections separated by dense neighborhoods in the City of Kenosha. The northern segment runs northeast from 35th Street in the city to 1st Street at the...
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,...
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...
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...
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...
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...
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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...
Ridgefield Trace currently consists of two short segments open for use. The western section runs from McHenry County College on US 14 in Crystal Lake to just west of N. Oak Street. Active railroad...
The Great Divide Trail sits is a one mile non-motorized trail through a negihborhood at the northern tip of Joliet, Illinois. The paved trail, which sits in the shadow of electric transmission lines,...
The Kuhn Road Trail starts on Lies Road, at Glenbard North High School and continues south along Kuhn Road, past single-family homes and Friendship Park. The trail officially ends at Barbara O'Rahilly...
The Pennsy Greenway is currently open in two segments between Calumet City, Illinois, and Schererville, Indiana. The northern portion begins at the southern end of the Burnham Greenway in Calumet City...
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The city of Joliet saw its electric utility corridors as a recreational opportunity. One such trail is the Fort Beggs Bike Trail, which starts on Theodore Street and heads northwest in the shadow of...
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...
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,...
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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....
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...
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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...
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...
Blackberry Trail follows a stretch of Blackberry Creek in Montgomery, Illinois. The trail is accessible from the forest preserve entrance at Caliendo Circle. Heading north, the trail reaches Mayfield...
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...
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...
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,...
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...
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...
Racine County's eastern edge is home to the MRK Trail, a rail-with-trail that extends north from the City of Racine to the Village of Caledonia. Because Racine County standardized its signs several...
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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...
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,...
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...
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...
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Racine’s southeastern neighborhoods are home to the North Shore Trail, which extends south to the Racine–Kenosha county line. Because Racine County standardized its signs several years ago, you won't...
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...
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...
The Hebron Trail rolls across the northern Illinois prairie through the former corridor of the Kenosha and Rockford Railroad, known as the Kenosha Division Line at the time of its demise in 1939....
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...
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...
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,...
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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....
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...
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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....
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...
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...
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...
Prospect Heights has very few sidewalks, so biking, inline skating or walking are moved to the streets or in the parks. Don't underestimate the Prospect Heights Bike Path which is over four miles of...
The Prairie Crossing Bike Path is a hard surface trail connecting Mundelein to Grayslake in central Lake County, Illinois. The trail is perpendicular to the 30-plus-mile Millennium Trail, which it...
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...
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...
Lake Renwick Preserve is home to an artificial lake of the same name that was created from former quarries where aggregates for concrete were once mined. Today, the lake is a recreational amenity in...
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,...
The city of Joliet saw its electric utility corridors as a recreational opportunity. One such trail is the Fort Beggs Bike Trail, which starts on Theodore Street and heads northwest in the shadow of...
Leave the cars at home: the Route 30 Bike Path gives users an alternative way to travel from the Village of Frankfort in the east, through Mokena to New Lenox in the west, a distance of over 7.5...
The Dunes Kankakee Trail is a 5.5-mile walking and bike path that It exists in 2 discrete segments: one that is 2.4 miles paralleling County Road 25 East, and the other segment east of that that is...
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...
The Thorn Creek Trail offers a paved route traversing woodlands abundant with wildlife through several communities on the southern outskirts of Chicago. The trail travels from Brownwell Woods in...
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...
Racine’s southeastern neighborhoods are home to the North Shore Trail, which extends south to the Racine–Kenosha county line. Because Racine County standardized its signs several years ago, you won't...
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...
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...
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...
Beautiful but cold ride with just a little snow on the trail and 22F. Saw a decent sized buck that ran in front of me down the trail for a mile. The trail is very well-maintained, at least the 15 miles I rode from Joliet.
Great trail! Well-paved without damage. Lots of trees and turns. Not boring and straight like many city trails. Thorn Creek travels through woods, meadows, and some suburbia. Watch your map so you don't end up going off on one of the many offshoots.
I started at the southern end in River Forest. The trail was a flooded mudpit despite the fact that it hasn't rained in ages, was covered in huge fallen tree branches, and just in overall disrepair. Then, just past Fullerton, the trail literally disappeared INTO the Des Plaines River, leaving you NO choice but to turn back around. You're literally no better off on this trail than you would be if you just started off randomly making your way through the forest.
I mostly ride the crushed Gravel from the Genoa City Parking area down to Petersen Park. The trail is well maintained, although some of the asphalt is in need of some TLC. All-in-All, it's a 5 star trail as is most of the trails in Illinois. The parking areas are well maintained and convenient with Bathroom facilities and water.
I have been riding this trail for 10 years now and it is awesome. I ride a MTB and a drop bar gravel bike and both are well suited for any conditions on this trail. I personally love to ride thru mud and water...it's just plain fun as is this trail.
I like this trail. Indiana is doing nice things for bikers/runners recently. You do have to stop at street crossings, but when you make it to the Whiting lakefront, it's worth it. Beautiful. It also passes a minor league baseball stadium and the mascot HOF.
I just wanted to update my review since the separation has (mostly) been completed. There are now 2 trails, one for biking and one for running. It definitely helps with the congestion. There are still some areas you need to pay attention to when the paths cross and you'll still come upon someone that is on the wrong path, but it's much better than it was.
I've ridden and run this trail several times. It's really nice, newly paved and smooth. Well taken care of and has nice views. The only warning is this trail can get pretty busy so be cautious on it.
I've rode nearly 90% of this trail and enjoyed 100% of it! Definitely not a paved trail as many have noted and a bit muddy in spots (West of Marseilles), you have to appreciate the awesome views this trail has to offer! Small towns spaced every 5-6 miles offer a rich historical past, shopping, dining, many parks, and a glimpse of life as it was back in the days. Plenty of nature to photograph so make sure you bring your camera. The trail can use some much needed maintenance in areas, while other spots offer a flat and firm surface. Recent trees that have fallen over the trail have been cut. At one section between Utica and Ottawa there is a bridge out, but a small wooden plank has been erected to navigate the small creek. Plan an all day ride and you will not be disappointed with the scenic views and fun this trail can offer!
The Great Western Trail is very close to my home so I ride this trail often. I park in different areas and take a spin out from there. The scenery goes from a canopy of woods to open farmland. On a very windy day the open farmland can be a bit of challenge for me. I park on Wooley rode off of Rt 47 and ride east to St Charles on windy days. Lots of woods and protection from the wind this direction so the ride is easier for me. A stop in Wasco is a must. Great café with good coffee and nice sandwiches. I park in Sycamore many times and ride to Woolley road and back. Great views of the Midwest farmlands. Each direction gives you a 20 - 22 mile ride. If you ride towards St Charles be sure and cross Dean Street into LeRoy Oaks Forest Preserve and see the wild flowers in bloom in early spring. Just beautiful. LeRoy Oaks Forest Preserve is at the end of the Great Western Trail at the eastern terminus.
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