Explore the best rated trails in Oswego, IL. Whether you're looking for an easy walking trail or a bike trail like the Old Plank Road Trail and Techny Trail. 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 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...
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 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 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...
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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...
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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...
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...
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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 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 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...
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 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 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 Struckman Boulevard Path is just over a mile long, stretching between Bartlett Road and State Route 59, (although the path narrows from the end of Sunset Park up to the end on SR 59). That said,...
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...
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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 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 9-mile Green Bay Trail runs parallel to Chicago's Metra commuter rail line north of the Chicago city limits. Stretching through North Shore towns such as Kenilworth, Winnetka, Highland Park and...
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...
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...
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...
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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,...
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 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,...
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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 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...
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 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 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 9-mile Green Bay Trail runs parallel to Chicago's Metra commuter rail line north of the Chicago city limits. Stretching through North Shore towns such as Kenilworth, Winnetka, Highland Park and...
The Cal-Sag Trail (or, Calumet-Sag Trail) is currently under active construction. It currently has a competed section of over 15 miles, stretching from near its western terminus at the John Husar I&M...
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...
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....
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...
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...
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 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 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...
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...
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 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 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 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 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 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 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 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 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...
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 9-mile Green Bay Trail runs parallel to Chicago's Metra commuter rail line north of the Chicago city limits. Stretching through North Shore towns such as Kenilworth, Winnetka, Highland Park and...
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 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 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 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...
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...
Ridgefield Trace currently consists of two short segments open for use. The western section runs from McHenry County College on US 14 in Crystal Lake to just west of N. Oak Street. Active railroad...
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,...
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,...
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...
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...
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.¿¿
Great walk! Wonderful scenery.
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.
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