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 93 trails covering 961 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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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 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...
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 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 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 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 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 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...
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...
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 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 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...
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...
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...
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 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 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 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,...
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 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 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 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 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 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 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 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...
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 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 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 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 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...
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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...
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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 DuPage River Trail spans nearly 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...
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 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 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 Union Pacific Recreation Path offers a short route through the Village of Lincolnwood's east side between Devon and Touhy avenues. Following the former Union Pacific Railroad, the rail-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...
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...
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 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 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 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 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 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 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...
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 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...
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...
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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 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 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...
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 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 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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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 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 Great Western Trail is very close to my home so I ride this trail often. I park in different areas and take a spin out from there. The scenery goes from a canopy of woods to open farmland. On a very windy day the open farmland can be a bit of challenge for me. I park on Wooley rode off of Rt 47 and ride east to St Charles on windy days. Lots of woods and protection from the wind this direction so the ride is easier for me. A stop in Wasco is a must. Great café with good coffee and nice sandwiches. I park in Sycamore many times and ride to Woolley road and back. Great views of the Midwest farmlands. Each direction gives you a 20 - 22 mile ride. If you ride towards St Charles be sure and cross Dean Street into LeRoy Oaks Forest Preserve and see the wild flowers in bloom in early spring. Just beautiful. LeRoy Oaks Forest Preserve is at the end of the Great Western Trail at the eastern terminus.
The Fox River Trail is a gem in so many ways. I usually park in Dundee or Geneva, IL. I can go north or south on the trail from either of these towns and get a 24 mile ride in. The towns along the way are just super for stopping for lunch, coffee, shopping and of course ice cream. The trails are so well maintained and there is a scenery change no matter what direction you go. I don't have a favorite direction each one is great. The Fox River is never too far away. I would recommend this trail to everyone and will continue to ride the trail as much as I can. The Fox River Trail also connects to the Illinois Prairie Path which takes you to another great town Wheaton. I park in South Elgin and ride south to connect to the Illinois Prairie Path. Wow! lots of places to eat in Wheaton. Hope everyone gets out and enjoys the Fox River Trail.
I try and ride this trail every spring. Great way to get your legs back in shape after a long winter in Illinois. I usually take the main loop around twice. I go one direction and then turn around and go the other way getting a look at the scenery both ways. The main loop is about 8 miles around so I end up getting 16 miles in. The scenery is nice and the trail is well maintained. You are hardly ever riding alone.
I use the southern most part of Trail from Bloomindale Ave up to Ohare mostly. Trail is great, views, water at groves is close, only negative is all dead wood after flooding. I t can sit and block trails for months until its removed.
The bridge that crosses the DesPlaines River at the east end of the trail (along Willow Springs Road) has been replaced and is now open.
2 WOMEN ATTACKED BY MAN WITH HAMMER ON CRYSTAL LAKE BIKE TRAIL 9/24/19 515pm7https://abc7chicago.com/2-women-reportedly-attacked-by-man-with-hammer-on-crystal-lake-bike-trail/5566978/
We rode the main trail and explored a few trails leading off the main trail on our mountain bikes. The only complaint is the lack of water. We are going back in a couple of days to do two loops and try more side trails. We will bring a cooler with our supplies
We came thru off of Batavia Rd and was an easy no traffic ride. Easy loop back to Prairie Path Trail. Headed north on Kirk and is under construction and west side bike trail is terrible going up to Faybian Pkwy.
We’ve spent many hours on this trail since we started riding a tandem two and a half years ago. We live close the Virgil Gilman trail in Sugar Grove and have spent most of our time on the southern half of the Fox River trail north and south of its junction with the Gilman Trail. The Fox River Trail also connects with the Illinois Prairie Path and its spurs as you venture north of Aurora through Elgin.
Six weeks or so ago we decided that we would try to ride the entire length of the trail and back. We spent the last couple of weeks on the northern section of the trail making sure that we knew our way through the northern half which has a few sections that go around short breaks in the paved trail such as north of State Street in South Elgin and heading south into South Elgin where the trail meets Raymond Street, there is also a junction to the Elgin spur of the Prairie Path. If you cross Raymond Street, you’ll be on the Prairie Path which you can use to go around South Elgin. To stay on the Fox River Trail, do not cross Raymond – go around the corner to the right. Each of these practice runs also included the hilliest section of the trail between South Elgin and Batavia. Tandems are crazy fast downhill due to the mass and aerodynamics but riding up long hills takes a special kind of love!
Yes, the trail can be busy around the towns; especially on weekends. The same reasons we are attracted to this trail also brings out the people walking and families. We thought doing our end to end ride would be better on a Friday but there were a surprising number of folks enjoying the beautiful day with us. We’re just patient with passing and give a thank you as we go by. More so than some other trails, there are many surface crossings so this trail will not boost your average speed, but we find these limitations to be a reasonable trade-off for this well-maintained trail.
The ride yesterday was generally incident free and went according to plan and was our longest ride to date on the tandem. We started out with a rear derailleur skipping issue which was very annoying (you shift more on a tandem than a single) but a quick adjustment at our first rest stop and all was well. The only other issue was a bridge replacement over Poplar Creek just north of South Elgin. Last Sunday there was no sign of construction, but we approached yesterday to find the trail closed. We checked it out to find that the old bridge had been removed but the new one was not yet installed. Fortunately, we found an unofficial detour and continued. Southbound, there was a sign that indicated the trail would be closed through the end of the month.
Loved exploring this trail today! A bit hillier than Prairie or Salt Creek but nice rolling up and down both ways. We easily found Sag Quaries with Google Maps off of 83 and jumped right on. Couldn't believe no street crossings all the way to Nicks BBQ at the end of the trail! We stopped for lunch than headed back. Nice 24 miles! Loved the Lake Katherine area and the low traffic on this trail! We'll do it again in the fall as the foliage will be beautiful!
I am embarrassed to admit that I have lived in the area for 20+ years and have driven by this little gem more times than I can remember. It is gorgeous!! I took my bike and was amazed at the number of trails and how large the area is. I went on a weekday afternoon so while many people were there walking their dogs or just enjoying the solitude, it never felt crowded. There were many stretches where I was completely alone and had the trail to myself. The parking lot of the Herrick Road entrance can accommodate many cars. It's a great oasis in the Western suburbs and I can't wait to go back!!
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