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 85 trails covering 926 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 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...
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...
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 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...
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 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 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 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...
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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....
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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...
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...
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 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,...
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 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 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 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 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 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 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...
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...
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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 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 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 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...
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...
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 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...
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 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 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 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 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 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 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 Stearns Road Bike Path is a dedicated sidepath traveling from Hanover Park to the Bartlett, in the Chicago suburbs. The asphalt path sits on the north side of Greenbrook Boulevard/ Stearns Road,...
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...
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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 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...
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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...
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 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...
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...
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 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 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...
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 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,...
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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 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...
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 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 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...
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...
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...
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...
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 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 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 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.
The Fox River Trail is a gem in so many ways. I usually park in Dundee or Geneva, IL. I can go north or south on the trail from either of these towns and get a 24 mile ride in. The towns along the way are just super for stopping for lunch, coffee, shopping and of course ice cream. The trails are so well maintained and there is a scenery change no matter what direction you go. I don't have a favorite direction each one is great. The Fox River is never too far away. I would recommend this trail to everyone and will continue to ride the trail as much as I can. The Fox River Trail also connects to the Illinois Prairie Path which takes you to another great town Wheaton. I park in South Elgin and ride south to connect to the Illinois Prairie Path. Wow! lots of places to eat in Wheaton. Hope everyone gets out and enjoys the Fox River Trail.
I try and ride this trail every spring. Great way to get your legs back in shape after a long winter in Illinois. I usually take the main loop around twice. I go one direction and then turn around and go the other way getting a look at the scenery both ways. The main loop is about 8 miles around so I end up getting 16 miles in. The scenery is nice and the trail is well maintained. You are hardly ever riding alone.
I use the southern most part of Trail from Bloomindale Ave up to Ohare mostly. Trail is great, views, water at groves is close, only negative is all dead wood after flooding. I t can sit and block trails for months until its removed.
The bridge that crosses the DesPlaines River at the east end of the trail (along Willow Springs Road) has been replaced and is now open.
We rode the main trail and explored a few trails leading off the main trail on our mountain bikes. The only complaint is the lack of water. We are going back in a couple of days to do two loops and try more side trails. We will bring a cooler with our supplies
We came thru off of Batavia Rd and was an easy no traffic ride. Easy loop back to Prairie Path Trail. Headed north on Kirk and is under construction and west side bike trail is terrible going up to Faybian Pkwy.
We’ve spent many hours on this trail since we started riding a tandem two and a half years ago. We live close the Virgil Gilman trail in Sugar Grove and have spent most of our time on the southern half of the Fox River trail north and south of its junction with the Gilman Trail. The Fox River Trail also connects with the Illinois Prairie Path and its spurs as you venture north of Aurora through Elgin.
Six weeks or so ago we decided that we would try to ride the entire length of the trail and back. We spent the last couple of weeks on the northern section of the trail making sure that we knew our way through the northern half which has a few sections that go around short breaks in the paved trail such as north of State Street in South Elgin and heading south into South Elgin where the trail meets Raymond Street, there is also a junction to the Elgin spur of the Prairie Path. If you cross Raymond Street, you’ll be on the Prairie Path which you can use to go around South Elgin. To stay on the Fox River Trail, do not cross Raymond – go around the corner to the right. Each of these practice runs also included the hilliest section of the trail between South Elgin and Batavia. Tandems are crazy fast downhill due to the mass and aerodynamics but riding up long hills takes a special kind of love!
Yes, the trail can be busy around the towns; especially on weekends. The same reasons we are attracted to this trail also brings out the people walking and families. We thought doing our end to end ride would be better on a Friday but there were a surprising number of folks enjoying the beautiful day with us. We’re just patient with passing and give a thank you as we go by. More so than some other trails, there are many surface crossings so this trail will not boost your average speed, but we find these limitations to be a reasonable trade-off for this well-maintained trail.
The ride yesterday was generally incident free and went according to plan and was our longest ride to date on the tandem. We started out with a rear derailleur skipping issue which was very annoying (you shift more on a tandem than a single) but a quick adjustment at our first rest stop and all was well. The only other issue was a bridge replacement over Poplar Creek just north of South Elgin. Last Sunday there was no sign of construction, but we approached yesterday to find the trail closed. We checked it out to find that the old bridge had been removed but the new one was not yet installed. Fortunately, we found an unofficial detour and continued. Southbound, there was a sign that indicated the trail would be closed through the end of the month.
Loved exploring this trail today! A bit hillier than Prairie or Salt Creek but nice rolling up and down both ways. We easily found Sag Quaries with Google Maps off of 83 and jumped right on. Couldn't believe no street crossings all the way to Nicks BBQ at the end of the trail! We stopped for lunch than headed back. Nice 24 miles! Loved the Lake Katherine area and the low traffic on this trail! We'll do it again in the fall as the foliage will be beautiful!
I am embarrassed to admit that I have lived in the area for 20+ years and have driven by this little gem more times than I can remember. It is gorgeous!! I took my bike and was amazed at the number of trails and how large the area is. I went on a weekday afternoon so while many people were there walking their dogs or just enjoying the solitude, it never felt crowded. There were many stretches where I was completely alone and had the trail to myself. The parking lot of the Herrick Road entrance can accommodate many cars. It's a great oasis in the Western suburbs and I can't wait to go back!!
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