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 89 trails covering 948 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 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...
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 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...
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 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 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...
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...
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....
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...
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...
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 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 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....
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 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 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 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 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...
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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...
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 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 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 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 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,...
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 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 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...
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 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...
Although just shy of two miles, the Veterans Memorial Trail provides a wooded, paved trail experience for residents in the Chicago suburbs of Romeoville, Lemont, and Woodridge. Those seeking a longer...
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 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 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...
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...
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...
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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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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 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...
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 trail system in Waterfall Glen Forest Preserve makes a loop around the entire park. The preserve is geologically significant, featuring glacier-carved rock ridges, ravines and wetland potholes,...
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...
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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 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 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 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...
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 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 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 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 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...
Although just shy of two miles, the Veterans Memorial Trail provides a wooded, paved trail experience for residents in the Chicago suburbs of Romeoville, Lemont, and Woodridge. Those seeking a longer...
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 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 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 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...
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,...
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 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 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...
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...
I love this trail. I was SO DISAPPOINTED that the trail was cut off at Willow Springs Road. Now I am wondering if the trail was open from 135th street to
Willow Springs Road.
I am also wondering what kind kind of promise is for the future.
Loved the ride. Few major road crossings but overall nice trail and not overcrowded at all
We enjoyed this trail. We had serpentineed our way from Wheaton to Batavia on the Prarie Path, were a bit tired and seeking a more direct route back. We left the Batavia Spur off the Fox River Trail, cut on a couple of neighborhood streets and entered Fermi on the Western side. (Kirk Rd and Pine Street) we weren't sure we were on a trail, (there was construction at the entrance)...but then we rode through the very interesting Fermi Labs. Nice easy paved trail on the side of the road. The trail took us to Batavia Rd which had a wide sidewalk for riding all the way to Butterfield Rd to pick the Prarie Path back up in Warrenville. A nice reprieve for our sore legs and enjoyable route!
Had my first ride on the IPP since moving to the western suburbs. I started on the main stem around Hillside, going west. Around Villa Park, I took the Wheaton Branch to Prince Crossing Rd, then picked up the Great Western Trail east, back to the main stem. Of the 37 miles I rode, about 95% was crushed limestone. Fortunately, for my first time out, I took a bike with larger tires and fenders. I came across quite a few puddles and muddy spots, and the larger tires handled the limestone well. I might be comfortable doing this ride on a 'cross bike, but I'm not sure how I'd feel taking my road bike out on it. I've seen enough of the Wheaton Spur already; way too many crossings. However, it would be a great stretch for a relaxing/recovery ride, with intensions of dining, or stopping for a beer or coffee. There are several spots one could pull off around Lombard or Glen Ellyn. I also noticed that large portions of that trail had smooth, paved, lightly trafficked roads running parallel to it. But, even managing to use roads whenever possible, all the stops and crossings break up the momentum. Hopefully, other branches of the trail have a more accommodating surface. Though for a crushed limestone path, it was pretty well packed.
Have to cross busy streets on this trail, but otherwise very nice for walking or riding a bike.
Too many damn trees and straight always. No trail markings. Started at essington/ingles and ended up by the starved rock dam...
The 1890’s working Farm is also a nice bonus including gift shop and modern rest rooms.
Took a early spring hike and path is wide and very easy to navigate. An occasional bench to sit, watch and reflect. Birds were everywhere. Some sightings were red headed woodpeckers, flicker woodpeckers, blue birds, blue jays, sand hill cranes, killdeer,,brown creeper, numerous red wing black birds and robins and many more birds I can’t name. Enjoyed taking the grassy trails that took us closer to water. A delightful place to visit!
We have been riding this trail every weekend for 10+ years. However, we took our first ride of the year for 2019 yesterday, and the trail is in bad shape. With the bridge out, there is no way to get on the Centennial Trail from Willow Springs. Is there a plan to repave the trail anytime soon?
I rode this trail yesterday while I had some time to myself. It was in the 30's, with a very light snow falling. That meant that very few people were out on the trail. That also meant it was a great day for a ride. I parked off of Golf Road next to the Black trail, rode south and did two loops on the red trail before returning to the car. The whole ride came to a bit over 17 miles. I probably saw as many animals as people. Three deer were grazing next to the trail, there were a couple of elk out in their fenced in area, and, most concerning, was coming around a corner and hearing an animal noise only to look over and see a skunk poised to spray me! Fortunately I was going past it, not at it, so I came away clean. Probably due to the lack of sun and my unfamiliarity with the Preserve, I never seemed to have a good sense of what direction I was riding. There were plenty of maps, but I just didn't get a feel for it. The environment varied quite a bit from prairie to forest. There had been a recent controlled burn, primarily in the woods, so there was a light smell of fire still in the air. It's definitely a great trail to ride when the people count is low!
The bridge crossing the Des Plaines River at the east end of the trail (Columbia Woods) is still closed. It was originally scheduled to be finished in October of 2018. Here is an update from IDOT:
"The bridge replacement over Des Plaines River in Willow Springs at Columbia Woods started in early summer 2018 and will be completed in late spring 2019. The project was initially delayed due to higher than normal water levels on the Des Plaines River which impacted reconstruction efforts. Also parts of the project were re-designed which effected the overall project timeline. Thank you for your patience."
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