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 Tall Grass Greenway Trail. With more than 102 trails covering 984 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 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 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 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 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 ComEd Greenway is an asphalt multiuse pathway running north-south through the village of Bollingbrook. The trail's name is an abbreviation of Commonwealth Edison, the name of the electric utility...
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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 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...
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 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...
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...
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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 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 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 DuPage River Trail spans over 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 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 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 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...
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 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...
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...
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...
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 Erie Lackawanna Trail connects Crown Point and Hammond, two former rail junctions whose early fortunes were tied to the tracks carrying people and goods to and from Chicago. Despite traveling...
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 Pennsy Greenway is currently open in two segments between Calumet City, Illinois, and Schererville, Indiana. The northern portion begins at the southern end of the Burnham Greenway in Calumet City...
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 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 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,...
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 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 Lily Cache Greenway travels east-west across Bollingbrook, from the ComEd Greenway to the Plainfield border. The trail more or less follows the course of its namesake creek, and is characterized...
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 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 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 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 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 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...
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...
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...
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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...
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 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...
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...
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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 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...
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...
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 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 Perryville Path runs nearly 7 miles, connecting the communities of Loves Park and Rockford, not far from the northern border of Illinois. A pleasant place to begin your journey is Rock Cut State...
Moraine Hills State Park Trail offers a wonderful experience for any geology or nature aficionado. A moraine is an accumulation of earth and stones carried and finally deposited by a glacier....
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...
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...
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 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...
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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 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...
Lake Renwick Preserve is home to an artificial lake of the same name that was created from former quarries where aggregates for concrete were once mined. Today, the lake is a recreational amenity in...
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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...
I grew up biking this trail so I’m very partial, but it was a great place to spend time outside, challenge myself, and explore. The fact that I could bike from my house to the DPR trail and have relatively safe access to so many forest preserves was fantastic. Quick stops off at independence grove to ride around the lakes or Dairy Queen to grab ice cream made it fantastic. Just rode again after not having visited in four years and it’s just as good as I remember, just have to watch for flooded underpasses in the spring (fun to ride through in the summer though when they’re flooded)
Good trail for walkers, runners, and bikers. Wore out other neighborhood routes so this was a nice surprise. Good number of people keeping appropriate distance.
Due to cancellation to a lot of road races I was able to run my virtual solo race to complete my Marathon yesterday. I felt safe running along this trail. Some of the paths was barricaded due to hazzards water damage from the lake but tor the most part it was passable. Thank you so much for the experience.
My family and I bike on this trail every Sunday, weather permitting. Our favorite is the yellow trail. It has a combination of paved and unpaved roads. It also has uphills, downhills, flat areas, curves, mud, and trees. Seeing deer in the yellow trail is not uncommon. It’s super fun!!!
It can get busy depending on what time you go. It also has a lot of debris at times as well
Beautiful but cold ride with just a little snow on the trail and 22F. Saw a decent sized buck that ran in front of me down the trail for a mile. The trail is very well-maintained, at least the 15 miles I rode from Joliet.
Great trail! Well-paved without damage. Lots of trees and turns. Not boring and straight like many city trails. Thorn Creek travels through woods, meadows, and some suburbia. Watch your map so you don't end up going off on one of the many offshoots.
The path between Bemis Woods in Western Springs to the Brookfield Zoo is great! Nicely paved and easy to ride. You have to cross a couple of busy streets, but most of them have traffic signals.
I started at the southern end in River Forest. The trail was a flooded mudpit despite the fact that it hasn't rained in ages, was covered in huge fallen tree branches, and just in overall disrepair. Then, just past Fullerton, the trail literally disappeared INTO the Des Plaines River, leaving you NO choice but to turn back around. You're literally no better off on this trail than you would be if you just started off randomly making your way through the forest.
I mostly ride the crushed Gravel from the Genoa City Parking area down to Petersen Park. The trail is well maintained, although some of the asphalt is in need of some TLC. All-in-All, it's a 5 star trail as is most of the trails in Illinois. The parking areas are well maintained and convenient with Bathroom facilities and water.
I like this trail. Indiana is doing nice things for bikers/runners recently. You do have to stop at street crossings, but when you make it to the Whiting lakefront, it's worth it. Beautiful. It also passes a minor league baseball stadium and the mascot HOF.
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