Explore the best rated trails in Chicago, 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 114 trails covering 4788 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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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...
Although just shy of three 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...
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 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...
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...
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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,...
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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...
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...
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 Marquette Trail is part of the Marquette Greenway, which will one day span more than 50 miles through Northwest Indiana, connecting communities along the southern shore of Lake Michigan. The...
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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...
About an hour northwest of Chicago, the beautiful Grant Woods Forest Preserve spans more than 1,000 acres, offering an outdoor respite of prairie, woodlands and marshes. The crushed limestone pathway...
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...
With farmland to the east and the Des Plaines River Floodplain to the west, this picturesque trail is a relaxing adventure on two feet or on wheels. The crushed stone trail runs from Prairie Springs...
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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...
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 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...
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,...
Lake Arlington is an artificial lake and popular recreation area in Arlington Heights in Cook County. The park features amenities to interest visitors of all ages and it is a local favorite for family...
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Although its current length is just over a mile, the small-but-mighty Chessie Trail will connect several parks in the northwestern Indiana city of La Porte. At its northern end, the paved pathway...
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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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...
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...
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 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...
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...
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...
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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...
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...
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....
Note: This developing route is not yet fully contiguous – it is just over 50% complete. Please refer to the Trail Map for more information on the existing sections of trail, as well as the online...
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 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...
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 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...
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 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 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 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...
With farmland to the east and the Des Plaines River Floodplain to the west, this picturesque trail is a relaxing adventure on two feet or on wheels. The crushed stone trail runs from Prairie Springs...
First-time visitors to the Oak Savannah Trail might be surprised at the profusion of natural areas they’ll encounter as they travel the 9.5 miles between Hobart and Griffith in northern Indiana’s...
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...
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...
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...
Lake Arlington is an artificial lake and popular recreation area in Arlington Heights in Cook County. The park features amenities to interest visitors of all ages and it is a local favorite for family...
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...
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...
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...
Helping to forge a connection between the northern and southern segments of the Kenosha County Bike Trail, the Kenosha Pike Bike Trail also has plenty to offer in its own right, giving trail users a...
Located in the west side of Illinois' second largest city, this flat, straight bike path sits on the side of Orchard Road. The trail passes by commercial, residential and natural areas, and crucially,...
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...
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...
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,...
The Illinois and Michigan Canal State Trail follows the eponymous waterway alongside the Illinois River. It traverses the I&M Canal National Heritage Corridor, designated in 1984 and the first...
The Vale Park West Pathway is a multiuse trail in the Chicago suburb of Valparaiso. At 0.7 mile long, the trail passes through a mix of woodland and prairie, as well as over a creek on a 220-foot...
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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 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 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...
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...
Although its current length is just over a mile, the small-but-mighty Chessie Trail will connect several parks in the northwestern Indiana city of La Porte. At its northern end, the paved pathway...
In the Chicago suburban area, the Salt Creek Trail, at 27 miles long, is a great trail for what I like to do, which is cycling wayfinding. It’s not a rail to trails so the trail stiches together a variety of different segments in different surroundings: paved paths in forest preserves, separate paths along highways, gravel paths, subdivision roads and even a wood chip path. There are many connecting paths, so don’t expect a sign for every turn and that’s where wayfinding comes in. Use your TrailLink downloaded map and find your way. I made a few wrong turns but that’s part of wayfinding. I parked at Edgewater Park and did out and back rides, first to the south and then to the north. A fine 54-mile ride on a beautiful fall day. I even found two updates that are needed to the TrailLink map, which I will send to Rails to Trails Conservancy.
I started from the south entry point and only made it a few miles in before deciding to just take the roads back south. It hadn't rained for a few days and the bridge underpasses were still full of pooled water and soft mud. I don't even know if I'd ride through them on a mountain bike unless I was really looking to get nasty.
The eastern side of this well maintained trail contains a wide variety of habitat including riverside, prairie, woodland, lakeside, wetland, and urban making this a 4 season ride. We biked through acres of golden rod in bloom which was just magnificent. The trail does get more urban traveling west and has intersections but does a good job of staying by the river.
Started out from Utica and rode to trails end in LaSalle. Trail was in fairly good shape, but needed weeds cut down. Went back to Utica and headed towards Ottawa. The trail was like an old maintenance road that had been neglected. Very tall weeds that prevented me in many places from seeing where I could ride. After going about two miles I turned around because I didn't feel safe. It's a shame that there is so little maintenance on what is a beautiful area.
This trail is awesome for a gravel bike ride. My hygienist drove me to the start and raced me on the road, I finished the trail just in time for lunch break and beat the hygienist's car!! Then I got back to my dental work so I can get paid and buy next year's Cervelo.
We rode the trail south from Hoff Rd. (Midewin Prairie trailhead) to the river yesterday. The repairs are finished, and it is a smooth ride with just a few soft spots. Crushed limestone has been added to the wooded area that was just packed dirt before. A bonus is that it's monarch migration season, and there are many along the trail by the prairie. The only negative is that the restroom at Hoff Rd. has been boarded up, so the only restrooms along that part of the trail are at Symerton and the forest preserve at Ballou Road.
The trail is closed at mile 6. There is little, if any signage for the detour. Take Old Elm Rd east to pick up the North shore trail to bypass the closure.
The "too big", loose stones make this trail almost unusable. Stay away. Your bike and body will thank you.
Trail was closed in a number of places & finding a ride around was impossible.
This trail is exactly as described. We even met horses in the trail. Good surface but on busy days one needs to give way to those not as respectful of others. Neat history along the way by the equestrian end of the trail.
I just rode from Custer Park 8 miles north for a round trip of 16+ miles, and didn’t encounter the loose stone mentioned in earlier reviews. Perhaps it settled because my ride was great. Only complaint is that I forgot my water bottle. Fortunately the Will Co Ballou RD Dog Park (2 miles north on the trail from Custer) has water fountains. This was my second visit to this trail over the past couple of years.
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