Find the top rated trails in Westchester, 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 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...
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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...
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,...
Prairies and dunes are just two of the natural features you’ll experience on the Prairie Duneland Trail, located just a few miles south of the Lake Michigan shoreline and the Indiana Dunes National...
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....
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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 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...
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 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,...
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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...
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 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 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...
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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 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 Dunes Kankakee Trail is a 3-mile walking and bike path that begins in the Indiana Dunes State Park and travels south to Chesterton. It connects the Calumet Trail, which is also in the state 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 Old Plank Road Trail travels nearly 22 miles between Chicago Heights and Joliet across a densely populated suburban landscape, where you’re never far from a café or espresso stand. Still, you...
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...
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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 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 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...
Prospect Heights Bike Path runs between Woodland Trails Park and Country Garden Park, paralleling the commuter rail tracks on its north–south leg. The trail provides a nice off-road route through the...
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...
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 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 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...
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 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 Illinois and Michigan Canal State Trail follows the eponymous waterway alongside the Illinois River. The trail runs along the old canal towpath from LaSalle to the historical quarry town of...
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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...
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 Cal-Sag Trail (or, Calumet-Sag Trail) is currently under active construction. As of early 2018, it has a competed section of about 13 miles, stretching from near its western terminus at the John...
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 Chesapeake and Ohio Greenway (also referred to as the C&O Trail) offers a short, paved route through Merrillville, a town just a few miles south of Gary and the southern tip of Lake Michigan. The...
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 Virgil L. Gilman Trail travels from quiet forest and prairie lands to bustling neighborhoods in just 11 miles, linking a woodsy community college campus with the eastern Chicago suburb of...
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 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 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 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 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 Illinois and Michigan Canal State Trail follows the eponymous waterway alongside the Illinois River. The trail runs along the old canal towpath from LaSalle to the historical quarry town of...
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...
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 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 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...
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The Veterans Memorial Bikeway begins in Hebron in northwestern Indiana’s Porter County. From there, it follows the diagonal route of the former Pennsylvania Railroad for just over 8 miles through Lake...
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 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 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...
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 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 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 Kenosha County Bike Trail is open in two sections separated by dense neighborhoods in the City of Kenosha. The northern segment runs northeast from 35th Street in the city to 1st Street at the...
The Cal-Sag Trail (or, Calumet-Sag Trail) is currently under active construction. As of early 2018, it has a competed section of about 13 miles, stretching from near its western terminus at the John...
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...
Prairies and dunes are just two of the natural features you’ll experience on the Prairie Duneland Trail, located just a few miles south of the Lake Michigan shoreline and the Indiana Dunes National...
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....
Won’t be riding this again on the road bike. Fumes from roads make this not so pleasant. Sculptures and play ground for kids are great but that’s about it. Got lost when it flips to other side of river. This route is for kids on bikes, not serious cyclists. Fun all the same with the kids for sure
Coming from the uk I was pessimistic about city cycling. After getting bored of the lake front trail and north Sheridan/Green Bay road repeats this trail is a god send. Love it. Perfect for road biking and quiet(midweek) will continue to look for other trails but this one will be hard to beat.
Rode mid April, the trail is all asphalt. Parking in Crown Point was easy. Many busy streets to cross.
Excerpted from my blog (https://desplainesrivertrailcycling.blogspot.com/)
April 12, 2018
First ride of 2018, 42 miles down and only 1,958 to hit my annual target! The afternoon started out warm and sunny, a rare occurrence this Spring as the start of April hasn't been this cold in Chicago in 137 years with multiple snow storms! About 90 minutes into my ride the wind shifted and it was like someone turned on an air conditioner - in five minutes the temp went from high 60's to 50 degrees which is where I usually draw the line on riding 'cause it gets too cold for me.
Overall trail conditions are pretty decent with no flooding from Deerfield Road up to Independence Grove and while the trail surface is somewhat rutted from the long winter it is in reasonably good shape. One word of caution, bring plenty of water as none of the wells along the trail are open for the season and are wrapped in plastic film.
I did the circuit around Independence Grove and from a distance spotted what appeared to be two baby owls peeking out of the hole in tree. I thought it was my lucky day and quickly snapped this pic (see on blog) only to get closer and realize they were fake, the dead giveaway is the yellow glue on their feet - fake news indeed :-)
Not much in the way of color on the trail yet, it has been too cold for any spring flowers.
I lived in Hammond in 2014-2016 and this was one of the nearby trails I would frequent. Very well maintained. It doesn't hit any unique spots or destinations. Just a fine trail for a road or touring bike.
This is the perfect trail in so many ways. Quieter, with water and restrooms, all sorts of native birds and animals, places to picnic and just enjoy the great outdoors. I feel lucky to have this trail just a couple blocks from my home on the south end. Summer here we come !
Nice flat trail , easy too access from different areas that’s a plus , only downside is too manny stops in Frankfort cross traffic, otherwise it’s a gem , a shout out too the Madison county trail in western Illinois 123 miles of trails really nice 👍
The trail is great for running, walking, and slow casual bike riding. If you are training for serious bike rides, I would avoid the trail between Crown Point and Griffith. The trail has serious cracks every 15 - 30ft that are harsh on a bike with 100psi tires. 17mph and the ride just hurts. The jarring is terrible.
Trail from Ridgeland Ave east to Cicero (2.5 miles) is paved.
Park at 131st and Cicero in Alsip has lots of parking spaces right beside the trail.
Trail east of here is in progress, with new bike/pedestrian bridge spans going into place last week at the East Arm of the Little Calumet River. This will provide a connection to Joe Lewis Golf course which will link to the Major Taylor Trail. Have no timeline for when that bridge will open.
My husband rode his fat tire bike on the trail this morning between Chestnut St., in Ottawa, and the Buffalo Rock trail parking lot. His goal was to check out the conditions of the trail. He said that it was not fun. He came back via the street. The trail was wet, and the 1/2 mile from Chestnut west, as well as the 1/2 mile from Buffalo Rock east had many piles of dog poop. (There is a parking lot at Buffalo Rock that people use when they walk their dogs.) Seems like the dog walkers do not even bother to sweep the poop piles to the side. That is the least you can do if you are not going to pick it up.
I visited this path on Summer 2017. I loved that path. My, my father and my nephews enjoyed all aspects of the path, the lakes, trees, animals and hills. As one of the visitor mentioned, this path offers a lot to see. We stopped once to see the entire colony of almost 100 turtles (Yes, we stopped long enough to count them) The view amazed us. Because the path follows "one way" only, it annoyed me a bit, but as we were exploring it, I understood the rationale. People had a reason to call it "Moraine Hills." Two way traffic would cause plenty of accidents. However, the those hills really shaped and strengthened our endurance. The step slopes would made simultaneously spit your lungs out on the way up, and on the way down scream from top of your lungs. Excitement and the joy from being on the path resulted in the best memories. Everyone needs to visit this path. I can assure you that I will come back there with pleasure.
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