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 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 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...
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 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 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,...
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 Ottawa Riverwalk begins downtown and heads northeast along the Fox River. In addition to offering beautiful views of the waterway, there are also boat launches and fishing spots along the...
The Millennium Trail is a planned 35-mile route through Chicago’s northern suburbs that will connect communities and forest preserves in northwestern Lake County. Currently, 28.5 miles of this...
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...
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 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...
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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...
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The western segment of the Great Western Trail in Illinois follows 17 miles of an abandoned railway corridor through DeKalb and Kane counties, between LeRoy Oakes Forest Preserve and the town 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 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 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 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 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 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 beautiful North Branch Trail is named for the North Branch of the Chicago River, along which it winds. At its northern end, the trail begins at the south end of the Chicago Botanic Garden and...
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 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 Virgil Gilman Trail travels through forest and prairie, from a quiet, rural community college campus all the way into suburban Chicago. The trail's namesake, Virgil Gilman,was director of the Fox...
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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...
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 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...
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 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...
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 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 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 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 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 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 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...
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 20-mile Old Plank Road Trail travels over the original Michigan Central Rail Road (MCRR) line, a railroad started about 1850 that ran from Lake Station in East Gary to Joliet. The rail was...
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 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 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 Illinois & Michigan Canal provided the final link in the water route from the east coast to the Gulf of Mexico by connecting Lake Michigan to the Mississippi River via the Illinois River. Today,...
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 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 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...
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 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...
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 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 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 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 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 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 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 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...
Located east of Lakeshore Drive, the Chicago Lakefront Trail is an 18.5-mile linear park along Lake Michigan that includes beaches, volleyball courts, playgrounds, baseball diamonds, tennis courts and...
Traveling along the Wauponsee Glacial Trail, you'll be surprised just how quickly you can move from an urban environment into the rolling fields of the Midwest. Starting in Joliet, within shouting...
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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...
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 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...
Great trail! Accessible, scenic and well-kept. I've lived walking distance from the trail for 20 years. It can be perfect walking, jogging and biking. We've enjoyed it for family outings with the kids when they were children. For safety, solo activities are best avoided as the trails can be isolated and very wooded in some areas. avoided for worecommend group outing
I rode most of the trail below Joliet on July 28 , 2017. Except for the closures shown on the DNR website (downtown Morris, Marseilles to Ottawa, and two bridges out near Utica), the trail was in decent condition. (I was glad I was on a hybrid and not a skinny bike.)
Joliet to Morris was in good shape. Some of this section is dull, some parts are pleasant.
The closure in Morris has been there for years, and the street detour is easy and not too long.
Morris to Seneca is my new favorite section: quieter and more woodsy than the rest. No trail problems.
Seneca to Marseilles was fine. There’s a good view of the Illinois River if you go a few blocks south of the trail in downtown Marseilles.
Marseilles to Ottawa was mostly dull and pointless. I went around the barricade just west of Marseilles and had to carry my bike over downed trees, which I expected. It got old after a while, though, and since the trail was boring at that point, I wish I hadn’t bothered. There’s a nice paved road next to the trail – use that instead.
Ottawa to Utica is in decent shape, except for the bridge that’s out, and I like this section. I went about 9 miles west from the Fox River aqueduct in Ottawa and came to the bridge. I was tempted to take my shoes and socks off and wade through the two inch deep stream and continue, but turned around instead. (It’s only another mile or so to downtown Utica).
I like the section below Utica, but with the bridge out, I didn’t feel like continuing.
If you accept the closures and the dull parts, the I&M is a good Illinois trail.
Southern 3 mile extension opening Saturday, August 12, at Foster and Kostner aves. Irene C. Hernandez Picnic Grove, LaBaugh Woods, Chicago.
Being a Chicagoan I had yet to ride the 606 until last week. My first impression was what a great trail. The idea of traveling without motor traffic and no stops for almost three miles flies by. The ride on the return trip was much slower as there was more traffic on The 606. Still it was the fastest way to travel through this area. The 606 has also improved an area that at one time the term less desirable would of been an understatement. The area has improved and the beauty of The 606 matches the surrounding homes and neighborhoods. This in my opinion is from The 606. We found all the people very pleasant on our journey and they seemed to be very proud of The 606. we saw the Chicago Police Department in a strong presence on our Saturday journey. The CPD was on both foot and bicycle. My only complaint is that it is too short of a trail. Hopefully Chicago will develop more of these useful neighborhood enhancing trails. It is all good on The 606.
Even before this trail connected with Wicker Park, I rode this trail often each summer, sometimes going to Griffith, sometimes about a mile short of the end, sometimes all the way to Griffith. I love this trail. I rode it for the first time in several years on 7Aug 2017, and hasn't changed much, except for a couple detours. And as a RR fan, love that it crosses Griffith Junction and with all the old cabooses, cars, etc.
I love this trail. Lots of shades, beautiful scenery, lots of animals like birds squirrels bunny's deer... Bears.... ;-) (just kidding about the bears). So.. yeah its an awesome trail. I will keep coming back here.
Love this path for a short week night ride after work. If you ride into the Kishwaukee Forest Preserve round trip is almost 6 miles. Prairie and forest with some hills that aren't too challenging on an asphalt path make it a great ride.
The 606 ultra-smooth surface is great for inline skating!
Popular with birders, bikers, or hikers, wildlife almost always on view. Northern end near eateries. Trail runs parallel to stream, ponds, and wetlands.
I often take this trail when I want to get places, not just as a way to spend some time outdoors. The trail connects directly with the West Branch Dupage River Trail, which then if you take north ~6 miles connects to the Illinois Prairie Path, which then connects you to basically everything. Additionally, the path goes through three of the best forest preserves in the region -- Springbrook Prairie, Greene Valley, and Waterfall Glen.
The section along 75th St east of Plainfield/Naperville Rd is somewhat narrow and not used a lot, but is made of crushed gravel and has a nice connection at Washington St via an underpass to the West Branch Dupage River Trail.
rode sw from Brandon Road lock. do not ride this trail on a road bike with anything less than 700x28. I flatted on one of the sections of loose gravel. The ride itself is pleasant enough in that area...lots of tree cover...but the canal itself is overgrown, and not what I expected as far as scenery goes
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