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 Prairie Point Trail is a scenic neighborhood route that connects twice to the longer Grove Road Trail. While never far from houses, the trail offers surprising scenery, including a stretch along a...
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 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 DeKalb Nature Trail provides a pleasant, tree-lined route in northern DeKalb. Near its western trailhead, it crosses the Kishwaukee River and passes through the Nehring Forest Preserve. Further...
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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 village of Palatine has connected many of its community assets with two long sections of off-road, multi-use trail. The more popular northern section is the one most references call simply and...
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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 Pennsy Greenway is currently open in three segments between Calumet City, Illinois, and Schererville, Indiana. The northern portion begins at the southern end of the Burnham Greenway in Calumet...
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 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 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 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 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...
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 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 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 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 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...
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....
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 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 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 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 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...
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....
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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 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...
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...
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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...
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 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,...
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 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...
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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....
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 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...
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 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 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 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...
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...
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 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 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 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 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 Kishwaukee Riverfront Path winds nearly 7 miles through downtown Belvidere, east of Rockford in northern Illinois. As its name implies, the paved scenic trail follows the waterway for most of its...
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 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 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 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 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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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...
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 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...
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 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...
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 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 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....
This is an amazing trail in the city I love. It’ll take you north to Hollywood st and south to the south short cultural center. North you can continue on the streets until hooking up with more trails all the way to WI. South is the same all the way to Indiana. But... ...it’s currently under construction. They’re separating the bike path from the runner/walking path so the trail is being worked on now. When it’s finished it will be magnificent. Just wanted to give you a heads up!
If you start in Algonquin I suggest parking in the park at the corner of Rt. 62 and Main St. I parked near the clock tower and had to ask a passing cyclist where to catch the trail. Once on the trail, the portion from Algonquin to Elgin is one of the best marked trails I've been on. It is very well maintained and passes through historic areas and scenic beauty. There were many walkers and joggers as well as cyclists. Also, there are plenty of quality rest areas along the way.
Solid 17 mile path for a decent workout. Fairly flat and well maintained. Follows highway IL 64 for the most part but does veer away in certain parts. Country and town mixed together. Excellent ride for the recreational biker who wants to get away but not to far away from civilization for a couple hours. Started and ended in Sycamore so there are easy amenities before and after the ride.
There’s the official path. While nice and paved, also has nice locally known paths. If you have a dirt/gravel capable bike, seek out the more challenging side trails. They are marked at the trailheads but the signage is hidden behind tall grasses and trees. Parts of the trails are visible via Google Maps Satellite view. Pro tip: bring mosquito repellent.
Great Sept evening spin, goldenrod, milkweed,rattlesnake master...
But to pause in pedalling made us mosquito fodder. Don't forget repellant!
I have walked this frequently and have had a lot of fun and excitement saw many deer and small animals chipmunks, squirrels and saw a couple of cardinals, I walk this once a day and have a good time met a lot of nice people while walking .
My husband and I rode this trail for the first time. We rode the Naperville and Bolingbrook sections many times. This section is as good. It has large portions with shade. Several toilets. Picnic tables. A dog park. Picturesque photo op trail branches. One drawback: dog poop. Strangly enough, not near the dog park. The poop is scattered 30 ft or so on either side of access points. No reason for it, because free bags are provided at each access point. Good thing dog walkers are too lazy to walk any farther. We will go back. The poop is not enough to keep us away. Also, we saw a police 🚔 patroling the trail.
I rode this trail to get my 100 mile ride in from Chicago. I liked it. The other reviews are true, it can be a little bumpy and there were a couple sections that could have been marked better but overall it was nice. There were places the trail seemed to split and I can’t wait to go back to explore where they go.
Remember the big flood? Tornadoes? This trail is maintained as well as possible considering our financial state in this state. The only real problem this year is the collapsed & under repair Morris viaduct that closed the trail. You must ride on the road to Stratton Park, then back on a continuous trail through Lockport. Safe from traffic, beautiful river views, professionally repaired washed out sections plus fairly responsive fallen tree removal keeps the trail ridable. Occasional trees down may require lifting bike over. I try to break off branches to clear a temp path till they cut it up usually withing a week or two.
Some shallow flooding occurs after heavy rains between Ottawa & Marseilles that is still ridable...Appox 2-4 in deep max.
All in all a wonderful fitness ride from Morris to Buffalo Rock.
I ride this trail every chance I get as I train for a triathlon. I ride my road bike on this paved trail and ride the unpaved Illinois-Mich Canal trail on the mountain bike. I am retired and ride multiple times per week.
Negatives: Somewhat rough in sections so I keep tires ~50psi for a smoother ride. Some tricky sections till you get to know the trail.
Positives (too many to list all): Good pavement in most areas, repaving is continuously fixing bad spots. Nice water refill stations plus drinking fountains, washrooms & repair stations with tools and pumps. No need to risk riding with traffic. Nice small climbing hills for a sprint challenge. Well shaded with nice woods & great river views. Very little traffic on weekdays. Weekends are fun & not too crowded. Oswego to Crystal Lake gives a round trip century ride.
These trails are the best in our nation for long fitness rides without mixing with traffic. I feel guilty riding these near empty trails alone. Where is everybody? ;))
The Crown Point section is now GREAT! Smooth new asphalt.
However, the Schererville section is horrendous! pouring a little tar into cracks for many years has not stopped the prolific and gaping cracks!! The Griffith and Highland sections also need repaving also, still a lot of cracks. The Schererville section needs REPAVING; it's the worst.
Maybe they need to stop the snowmobiles on the trail, the quad runners, and the service vehicles from driving on the pavement!
It used to be skateable for roller blades. Now we can't even stand to ride road bikes or a recumbent trike on the trail. Wrist and rear hurting cracks that jar your teeth they hit so hard.
The Cat3 wannabe's still ride on it as there are no bike lanes in Northwest IN to be out on the streets and the people in vehicles expect you to ONLY be on a trail.
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