Explore the best rated trails in Crestwood, 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 96 trails covering 961 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 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...
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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....
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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...
Note: Erosion caused by surging waves off Lake Michigan has caused the trail to collapse in sections. The eastern half of the trail along Lake Michigan is closed indefinitely. See the Chicago Park...
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...
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 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...
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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...
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...
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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...
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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 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...
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 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...
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...
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...
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 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 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...
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...
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...
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...
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...
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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...
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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,...
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...
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 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...
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 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...
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....
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 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 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...
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...
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 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,...
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The Fort Beggs Bike Trail (North) is a nearly mile-and-a-half long trail in Plainfield, Illinois. The trail shares the electric utility right-of-way, stretching from Fort Beggs Drive south to Spring...
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...
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...
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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 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 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...
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...
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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 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...
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 Preservation Path is a two-mile paved trail in the community of Matteson, Illinois. The path begins on Vollmer Road and terminates at the Old Plank Road Trail. The trail is paved with center...
The Fort Beggs Bike Trail (North) is a nearly mile-and-a-half long trail in Plainfield, Illinois. The trail shares the electric utility right-of-way, stretching from Fort Beggs Drive south to Spring...
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 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 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 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...
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 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...
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,...
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...
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 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 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...
I think this is a very good trail. It’s very scenic, especially compared to the dull eastern leg of the Great Western Trail. Its generally an easy ride with few hills. It is tricky in spots to navigate as the signage is not always clear. So review the path before you go and stop to review if needed en route. In Wood Dale, I recommend staying on Prospect until you pick up the bike route at Forest Preserve Drive or vice versa if coming from the south. This avoids the poor quality path to the bridge over Irving Park Road.
Biked this trail for the first time and it was great. I started at mile 29 and went north to mile 17. Took a break at Independence Grove. Nice picnic shelter and tables beside the pond. It was also my first time on crushed gravel and it’s definitely more physically demanding than pavement!
Pretty cool trail, not too much uphill or downhill. Perfect for speed riders like me. Simple as this, if you like to ride then ride, 26 miles makes it perfect. Go for it!
I'm pretty new to the area and haven't read all the other reviews here, but have enjoyed riding portions of this trail and will finish the whole thing soon. If you ride at night it gets dark because most of it is unlit wooded areas and there are few street lights. Only complaint is that as of Summer 2020, there are quite a lot of tree roots buckling the asphalt and even broken through in some spots. I have a road bike and any cycling enthusiasts know how harsh it can be to hit those anywhere above 15 mph without big tires or a suspension. There are also some bridges with uneven planking that will make you feel like you're dual-wielding two machine guns as you cross. A great trail overall but road bikes are in for a mild thrashing.
I recently walked this trail, and I loved every moment of it. The scenery is great and I have seen people fishing, taking pictures, and talking as they walk.¿¿
There is limited parking at the south end of the trail, as they have torn out the park to build condos. There is more parking, with a porta potty, a little ways north on IL Rt 25. Otherwise, the trail is superb in the south section. I have ridden every section south of Algonquin, and except for small portions where the pavement needs some work, and the bothersome on-road sections, this is a wonderful trail to ride.
I recently rode the trail south from Indiana Welcome Center. The pavement has developed deep bone-jarring cracks that are bad enough to potentially damage wheels. It's especially bad south of downtown Griffith. I recommend you avoid until they rehabilitate what otherwise would be an enjoyable ride.
This is a nice smooth trail for all types of bikes, but it's hard to find and follow. And you'll run into construction on Calumet Avenue in Indiana.
Best Trail in northern chicagoland by far. you get a taste of the woods, the suburbs, wild life ... and the cherry on top is the Botanic Garden. Ride Safe.
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