Explore the best rated trails in Oswego, IL. Whether you're looking for an easy walking trail or a bike trail like the Illinois & Michigan Canal State Trail and ComEd Greenway. With more than 103 trails covering 993 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 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...
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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....
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 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...
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 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 Kishwaukee-Kiwanis Trail winds through the northern Illinois town of DeKalb, coursing along a river, through woodlands, among open spaces through parks and through suburban back yards. The trail...
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...
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,...
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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 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...
The North Shore Channel Trail extends from the junction of Green Bay Road and McCormick Boulevard in northern Evanston to the junction of Lawrence Avenue and Francisco Avenue in Chicago. All but 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...
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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...
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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 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 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...
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...
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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...
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 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 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...
This shared-use path runs east-west through the village of Carol Stream in Du Page county. Sitting on the grassy north side of Lies Road between Fair Oaks Road and Gary Avenue, the path is used as an...
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 Bartlett Trail is a recreational trail in the Village of Bartlett, Du Page county. Though short, the trail is conveniently located as a space for exercise, while providing a safe route to school...
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...
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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 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 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 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 North Shore Channel Trail extends from the junction of Green Bay Road and McCormick Boulevard in northern Evanston to the junction of Lawrence Avenue and Francisco Avenue in Chicago. All but 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 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 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 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 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...
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 Four Sisters Bike Path forms a horseshoe around the northern end of Rochelle, a small city south of Rockford in northern Illinois. The path connects several schools and parks, and the city has...
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...
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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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...
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 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 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,...
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 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 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...
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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 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 Ottawa Riverwalk runs directly beside the beautiful Fox River, just north of its confluence with the larger Illinois River. It's a tranquil walkway with river views along its entire length. To...
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...
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 Four Sisters Bike Path forms a horseshoe around the northern end of Rochelle, a small city south of Rockford in northern Illinois. The path connects several schools and parks, and the city has...
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 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...
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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 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 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,...
Swanson Park Recreation Path is sometimes known as the Cherry Valley Path as it's located in the Village of Cherry Valley on the outskirts of Rockford in northern Illinois. The paved path travels...
Agree with all the posters below: this is a great trail and another example of what gems these FPD trails are! So close to urban, highway, and residential, yet a secluded ride in the woods.
If riding south and west, park at the Red trailhead at Lansing Woods, just east of Torrance on 183rd Street. Late season and winter, mind the wind direction before choosing which way to ride this trail, as much of it runs due south.
11.8 miles to the end of the red trail, then you can tack on 4 miles on the black loop. 11.0 miles to the east end of the Old Plank Road trail.
I went on a walk/roll with my husband on this beautiful trail. The Fall colors were enchanting. He was able to get my wheelchair through the path without a problem. I love the wooded pathway and all of the beautiful trees and scenery.
Best work out I had in a long time, I have been going for a moth + I love the u hills and the terrain is perfect.
This is a great trail for kids. My son and I went rollerblading. The trail is flat, so no big hills to manage. We had an awesome time!
We rode this trail today and loved the beautiful fall colors! We started at Danada off of Naperville Rd....loved the scenery, trail width and Herrick Lake! We then connected to Blackwell Forest Preserve via Butterfield for a longer ride (turning in just past Winfield Rd) Blackwell was beautiful, too! We found Two Brothers in Warrenville for lunch but used the GPS to find that and jump back on trail. 20 mile round trip...a great day!!!
I like the north branch of the trail for its beauty and the south branch for the rough ride and challenges. (Some nice scenery on the south branch too.) I have a 29er mountain bike. When I rode the south branch on my hybrid the first time I took that trail I had to take the bike in for repair afterwards. But on a mountain bike the south branch is a blast. Where else in the suburbs can you get a ride like that?
We started at Gebhard Woods State Park. Lovely day for a fall ride. There was a big sign telling us how far to ride to Seneca or Channahan, etc. we chose to ride to Channahan: however barely a half mile down the road there was a fence and there was no way around it. So we went toward Seneca...the trail was crushed gravel and grass and narrow but easy to ride. Might be a challenge to pass for newer riders, but it was a fairly flat ride and wooded. We enjoyed the ride. We rode from the state park on the roads to downtown Morris (which was lovely) after our trail ride. Took about 5 minutes to ride there.
I hesitate to write a review as of this well maintained trail because it's our "go to" on busy bike trail weekends where it remains relatively empty particularly on the east side. Relatively flat the trail follows the banks of the Des Plaines river and Sanitary and Ship canal. This bankside forested path is broken up by some water based industry that is also unique to observe.
On the north end of this well maintained trail you would not know your in the heart of a vibrant metropolitan city. At the north end be sure to add the Dan Ryan Woods circle path to extend your ride. As you ride south the landscape varies to urban in a favorable fashion. There's even a mead tasting room on the trail.
if you don't know about Major Taylor please look him up, as others have said, an American hero.
Have rode this trail 6 times and love it great surface to ride on trail is very well used and maintained very well . lol
We just moved to Lindenhurst at the very beginning of the trail. I have many parts of the trail out of Volo when we stayed at Fish Lake Beach in our motorhome. I am a senior rider. The trail had lots of wildlife and lots of wildflowers.
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