Find the top rated trails in Oswego, 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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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...
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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 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 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 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 Kishwaukee River Recreation Path runs for 2.5 miles in Cherry Valley on the outskirts of Rockford in northern Illinois. The well-maintained, asphalt trail connects the Kishwaukee River Forest...
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,...
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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...
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...
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 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...
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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 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 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...
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,...
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...
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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 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....
The Chain O' Lakes Bike Path is a paved trail that runs between E. Grand Avenue in Fox Lake and Grant Woods Forest Preserve to the east. The trail parallels the railroad track and Rollins Road/CR 31,...
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 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...
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 Chain O' Lakes Bike Path is a paved trail that runs between E. Grand Avenue in Fox Lake and Grant Woods Forest Preserve to the east. The trail parallels the railroad track and Rollins Road/CR 31,...
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...
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 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 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 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...
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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...
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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 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,...
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...
The DeKalb-Sycamore Trail—also known as the Peace Road Trail—parallels the eastern side of Peace Road from DeKalb to Sycamore in northern Illinois. Along the way, you'll pass a mixture of residential...
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....
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 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 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 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...
Baumann Park is adjacent to the Kishwaukee River in Cherry Valley, a community on the outskirts of Rockford in northern Illinois. A paved pathway runs through the park and loops around Baumann 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...
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 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...
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 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...
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...
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...
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...
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...
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 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...
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,...
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...
The H.U.M. Trail (a.k.a. the Huntley-Union-Marengo Trail) was planned to link all three of its namesake northern Illinois towns, but so far only connects Marengo and Union. Interestingly, the...
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...
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 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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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 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 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...
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
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.
Rode mid April, the trail is all asphalt. Parking in Crown Point was easy. Many busy streets to cross.
Excerpted from my blog (https://desplainesrivertrailcycling.blogspot.com/)
April 12, 2018
First ride of 2018, 42 miles down and only 1,958 to hit my annual target! The afternoon started out warm and sunny, a rare occurrence this Spring as the start of April hasn't been this cold in Chicago in 137 years with multiple snow storms! About 90 minutes into my ride the wind shifted and it was like someone turned on an air conditioner - in five minutes the temp went from high 60's to 50 degrees which is where I usually draw the line on riding 'cause it gets too cold for me.
Overall trail conditions are pretty decent with no flooding from Deerfield Road up to Independence Grove and while the trail surface is somewhat rutted from the long winter it is in reasonably good shape. One word of caution, bring plenty of water as none of the wells along the trail are open for the season and are wrapped in plastic film.
I did the circuit around Independence Grove and from a distance spotted what appeared to be two baby owls peeking out of the hole in tree. I thought it was my lucky day and quickly snapped this pic (see on blog) only to get closer and realize they were fake, the dead giveaway is the yellow glue on their feet - fake news indeed :-)
Not much in the way of color on the trail yet, it has been too cold for any spring flowers.
I lived in Hammond in 2014-2016 and this was one of the nearby trails I would frequent. Very well maintained. It doesn't hit any unique spots or destinations. Just a fine trail for a road or touring bike.
This is the perfect trail in so many ways. Quieter, with water and restrooms, all sorts of native birds and animals, places to picnic and just enjoy the great outdoors. I feel lucky to have this trail just a couple blocks from my home on the south end. Summer here we come !
Nice flat trail , easy too access from different areas that’s a plus , only downside is too manny stops in Frankfort cross traffic, otherwise it’s a gem , a shout out too the Madison county trail in western Illinois 123 miles of trails really nice 👍
The trail is great for running, walking, and slow casual bike riding. If you are training for serious bike rides, I would avoid the trail between Crown Point and Griffith. The trail has serious cracks every 15 - 30ft that are harsh on a bike with 100psi tires. 17mph and the ride just hurts. The jarring is terrible.
Trail from Ridgeland Ave east to Cicero (2.5 miles) is paved.
Park at 131st and Cicero in Alsip has lots of parking spaces right beside the trail.
Trail east of here is in progress, with new bike/pedestrian bridge spans going into place last week at the East Arm of the Little Calumet River. This will provide a connection to Joe Lewis Golf course which will link to the Major Taylor Trail. Have no timeline for when that bridge will open.
My husband rode his fat tire bike on the trail this morning between Chestnut St., in Ottawa, and the Buffalo Rock trail parking lot. His goal was to check out the conditions of the trail. He said that it was not fun. He came back via the street. The trail was wet, and the 1/2 mile from Chestnut west, as well as the 1/2 mile from Buffalo Rock east had many piles of dog poop. (There is a parking lot at Buffalo Rock that people use when they walk their dogs.) Seems like the dog walkers do not even bother to sweep the poop piles to the side. That is the least you can do if you are not going to pick it up.
I visited this path on Summer 2017. I loved that path. My, my father and my nephews enjoyed all aspects of the path, the lakes, trees, animals and hills. As one of the visitor mentioned, this path offers a lot to see. We stopped once to see the entire colony of almost 100 turtles (Yes, we stopped long enough to count them) The view amazed us. Because the path follows "one way" only, it annoyed me a bit, but as we were exploring it, I understood the rationale. People had a reason to call it "Moraine Hills." Two way traffic would cause plenty of accidents. However, the those hills really shaped and strengthened our endurance. The step slopes would made simultaneously spit your lungs out on the way up, and on the way down scream from top of your lungs. Excitement and the joy from being on the path resulted in the best memories. Everyone needs to visit this path. I can assure you that I will come back there with pleasure.
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