Explore the best rated trails in Winnetka, 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 121 trails covering 4852 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 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 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...
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 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...
Helping to extend the excellent network of trails around the city of Racine deeper west into the heart of the county, the Racine County Bike Trail serves as a disconnected addition to the...
The Racine-Sturtevant Trail runs for 3.5 miles from the western side of Racine to near the eastern edge of the Village of Sturtevant. The trail occupies an abandoned rail corridor for most of its...
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 Great American Rail-Trail highlights some of the country’s most iconic landmarks, well-known geography and storied history across a 3,700-miles-plus route between Washington and Washington....
The Root River Pathway uses a combination of off-road trail and on-road route to form a crescent around the City of Racine. The trail closely follows the bends of the Root River, making it a great...
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...
The Fort Hill Bike Path trail sits on the north side of Peterson Road/ County Road 20. The trail peels away from the Prairie Crossing Bike Path at Midlothian Road and extends west, passing industries...
Closure Notice: As of April 2021, the portion of the bike path on the Route 176 bridge over the Des Plaines River is closed for bridge repairs. Trail users can follow posted detour signage via the Des...
The John Husar I&M Canal Trail is the northernmost trail developed on the Illinois & Michigan Canal National Heritage Corridor. The Illinois & Michigan Canal provided the final link in the water route...
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 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...
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...
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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...
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...
Located in the west side of Illinois' second largest city, this flat, straight bike path sits on the side of Orchard Road. The trail passes by commercial, residential and natural areas, and crucially,...
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 Pike River Pathway is a paved, multi-use trail that runs along both sides of the reconstructed Pike River through the Village of Mount Pleasant and unincorporated parts of Racine County. The path...
Closure Notice: As of April 2021, the portion of the bike path on the Route 176 bridge over the Des Plaines River is closed for bridge repairs. Trail users can follow posted detour signage via the Des...
The Pennsy Greenway stretches between Calumet City, Illinois, and Schererville, Indiana. The trail begins at the southern end of the Burnham Greenway on the eastern edge of the Forest Preserve...
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 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 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...
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 Preservation Path is a two-mile paved trail in the community of Matteson, Illinois. The path begins on Vollmer Road and terminates at the Old Plank Road Trail. The trail is paved with center...
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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 13.5-mile Lake Michigan Pathway keeps you in close touch with the sixth-largest freshwater lake in the world as it links rail-trails north and south of the port city of Racine. Along the way, the...
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 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 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 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 WE Energies Trail, so named because it uses a Wisconsin Energy Corporation utility corridor for much of its route, links Racine and Oak Creek in Racine and Milwaukee counties. Despite the presence...
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...
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 Racine-Sturtevant Trail runs for 3.5 miles from the western side of Racine to near the eastern edge of the Village of Sturtevant. The trail occupies an abandoned rail corridor for most of its...
The DuPage River Trail spans over 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 and...
Although just shy of three 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...
Leave the cars at home: the Route 30 Bike Path gives users an alternative way to travel from the Village of Frankfort in the east, through Mokena to New Lenox in the west, a distance of over 7.5...
The Palos Heights Bike Trail offers a north-south route through residential and commercial areas on the west side of the community. It's also a key connector between two regionally important...
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 Preservation Path is a two-mile paved trail in the community of Matteson, Illinois. The path begins on Vollmer Road and terminates at the Old Plank Road Trail. The trail is paved with center...
The 13.5-mile Lake Michigan Pathway keeps you in close touch with the sixth-largest freshwater lake in the world as it links rail-trails north and south of the port city of Racine. Along the way, the...
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 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 Cal-Sag Trail (or, Calumet-Sag Trail) is currently under active construction. It currently has a competed section of over 15 miles, stretching from near its western terminus at the John Husar I&M...
Helping to forge a connection between the northern and southern segments of the Kenosha County Bike Trail, the Kenosha Pike Bike Trail also has plenty to offer in its own right, giving trail users a...
The Bartlett Trail is a recreational trail in the Village of Bartlett, Du Page county. Though short, the trail is conveniently located as a space for exercise, while providing a safe route to school...
The Pennsy Greenway stretches between Calumet City, Illinois, and Schererville, Indiana. The trail begins at the southern end of the Burnham Greenway on the eastern edge of the Forest Preserve...
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...
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 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 city of Joliet saw its electric utility corridors as a recreational opportunity. One such trail is the Fort Beggs Bike Trail, which starts on Theodore Street and heads northwest in the shadow of...
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...
Rode early May and a section south of Elgin was torn up and destined for replacement. No Detour signs seen. A worker alleged all repaired by mid month. Any update on this?
Easy flat trail that is very well maintained. Lots of stops to cross busy streets but many people stop their cars to let us cross. The trail mostly goes behind houses and neighborhoods.
I am always on this trail it’s perfect for long distance riding because you hit so many towns. I’m usually riding Frankfort Matteson Park Forest and Chicago Heights which is fun but only complaint is winter when the snow covers trail up but otherwise perfect trail.
Great asphalt trail with minimal intersections. Could use a bit of a resurface in some areas though.
Only did about 5 miles starting in Carpentersville near Main Street Bicycles and rode south for a bit towards Elgin. Stopped on our way back in Dundee at Diamond Jim’s for lunch. Was a fun day! Beautiful trail along the river, a lot of shade because most of it is wooded along the way.
Nice easy ride. Only gravel part is from Colonial Park to Lincoln Park.
Rode the OPRT for the second time yesterday (4/25), covering 31 miles from Western to Cedar and back.
Most importantly, it's a great ride through the far south suburbs - easy to access at several points and with Frankfort more or less midway-ish if you want a break to eat or drink. Also, the trail is almost completely straight and flat, not counting a few moderate climbs for overpasses and some stretches of *very* gradual incline or decline. A few areas with root-bumps in the trail, I've seen better and worse in this regard.
This may be unique to our chosen days of riding, but we have found the OPRT to be a very windy trail. There is a fair amount of tree and brush cover, but also large open areas (including one area where you traverse a large pond on a narrow causeway). Our first ride was last November, this time mid-spring. So, granted, spring and fall can be turbulent weather seasons. But both times the trail was so windy, we decided it would be a great place to return on one of those 90-degree summer days! Your mileage may vary on this issue.
Also, strangely, we encountered FOUR motor vehicles on the trail yesterday - three cars and one trail bike. All were east of Frankfort, and the three cars were near Western where we parked. One parked, one idling, and one moving - ahead & away from us. Haven't seen anything like this on other trails, other than an occasional vehicle doing trail maintenance; this was not that. The trail is clearly posted, no motor vehicles, so these folks were just flouting the rules. Again, don't know if this is common on OPRT but we didn't see it the first time. At one point we were BETWEEN the parked and idling cars, which felt a little hinky. But no issues, we weren't accosted, etc. Just a few individuals using a resource for its other-than-intended purpose.
This trail is close to my home and so easy to walk. Beautiful views of random artwork and the city. Will be my go-to when I need to be outside.
Good workout due to the many hills, maybe not for beginners but not too advanced either. A lot of people walking but fairly wide trail. I went counterclockwise from the Lemont parking lot so it’s more downhill at the beginning and more uphill towards the end.
This is my go-to trail. It's a straight shot, and fairly open to the wind and sun, but I love it for the meditational aspects. There's light traffic on the trail and crossroads (and better yet, bridges over some crossroads). This lets my mind wander and enjoy the ride. I love to start at Wasco and ride west out-and-back toward Virgil and Sycamore.
I rode the north end of this trail three years ago. It was very enjoyable and I would give that ride 5 stars. Ever since, I've looked forward to riding the south section.
I made the trip on Easter Sunday. I started at the trailhead at the NE corner of Midewin off Hoff Road. From there, I rode south, a 25 mile out-and-back to Custer Park. Pros: beautiful weather, interesting little towns, wide open vistas, light traffic, friendly folks, Kankakee River bridge. Con: the trail remembers everything that traversed it when it was wet and soft. There were petrified bike tire ruts, snowmobile/washboard tracks, deer hoofprints, bootprints, etc. In addition, as others as mentioned, there are a few soft spots, but worst of all, a verrry rocky section along Midewin. The ride was a boneshaker and I spent way too much time looking at the trail instead of the scenery. The south section could be a 5-star section, too, but based on the rough surface, I give it 3 stars.
Will County FPD says they're making improvements: https://www.reconnectwithnature.org/News-Events/News/Limestone-Screening-Work-Begins-on-Two-Mile-Sectio . Hopefully future riders have smoother experiences!
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