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 116 trails covering 1100 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 Lake Geneva Bike Path runs through the scenic resort city, offering connections to many of the community’s amenities. The trail has five unique, color-coded segments. The Blue Route is the...
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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 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 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...
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 Stearns Road Bike Path is a dedicated sidepath traveling from Hanover Park to the Bartlett, in the Chicago suburbs. The asphalt path sits on the north side of Greenbrook Boulevard/ Stearns Road,...
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 Erie Lackawanna Trail connects Crown Point and Hammond, two former rail junctions whose early fortunes were tied to the tracks carrying people and goods to and from Chicago. Despite traveling...
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 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...
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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...
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,...
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...
Turkey Creek Trail is a short but sweet walk or ride through the beautiful Ivan Gatlin Nature Preserve in the northwestern Indiana community of Schererville. This wetland area provides the opportunity...
Racine County's eastern edge is home to the MRK Trail, a rail-with-trail that extends north from the City of Racine to the Village of Caledonia. Because Racine County standardized its signs several...
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 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 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 White River State Trail is composed of two separate segments: a 12-mile stretch that runs between Elkhorn and just west of Burlington in Walworth County, and a 7-mile section that connects the...
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...
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...
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...
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 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 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 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...
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...
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 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 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 Seven Waters Bike Trail is a scenic corridor stretching more than 17 miles northsouth between Burlington and Muskego Lake into Waukesha County. The trail was originally three trails, locally...
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 Iron Horse Heritage Trail in Portage, Indiana, runs for over 2 miles between Max Mochal Road (SR 149) at the east end and Hamstrom Rd. at the west end. The trail passes through a greenway corridor...
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 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 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...
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 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 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...
The Dunes Kankakee Trail is a 5.5-mile walking and bike path that It exists in 2 discrete segments: one that is 2.4 miles paralleling County Road 25 East, and the other segment east of that that is...
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Racine’s southeastern neighborhoods are home to the North Shore Trail, which extends south to the Racine–Kenosha county line. Because Racine County standardized its signs several years ago, you won't...
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...
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 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...
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 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 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 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 Stearns Road Bike Path is a dedicated sidepath traveling from Hanover Park to the Bartlett, in the Chicago suburbs. The asphalt path sits on the north side of Greenbrook Boulevard/ Stearns Road,...
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 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 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...
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...
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...
The Iron Horse Heritage Trail in Portage, Indiana, runs for over 2 miles between Max Mochal Road (SR 149) at the east end and Hamstrom Rd. at the west end. The trail passes through a greenway corridor...
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 Marquette Trail offers picturesque views of Lake Michigan as it travels through the Indiana Dunes National Lakeshore. This scenic route follows an abandoned rail line through a variety of diverse...
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 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...
I have to agree with the previous reviewer in that this trail is not a destination in itself but does connect two very good trails. Leroy Oaks on the south end is very nice and worth some time (yes the bridge is rough, it has always been that way, I often wonder why). If you make the loop through St Charles using the Fox River Trail it’s a nice 15 or so mile trip.
I agree with the reviews of the trail south of Lake Cook Rd. It’s ok for a few miles south but there’s a notable difference of trail conditions from the trail north. Two different counties and budgets to maintain them, I assume. Traveled this trail multiple times this past COVID season. It’s my first year biking in 40 yrs and wow, what a great trail.
Runs along the river. The park is nice but the trail seems a little dirty with trash around the sides. There are multiple benches along the trail for resting. Not a bad trail, but not a very pretty trail either. So if you’re looking for some sight-seeing as you run then this may not be the ideal spot to run.
This trail is the beat I’ve ridden on. I’m new to biking but this trail, so far, is my favorite. Paved the entire way or off roading choice if you’d like as well. I like to mix it up a bit.
Started at Fairfield and 176 (waconda). Ample parking but not that crowded. Went north past the dog park through some gentle turns and inclines. Beautiful ponds along the way with plenty of benches along the way to stop and rest Went all the way to Ray’s and looped back around with a total of about 8-9 miles It is our go to trail for fresh air They also have a two other trails there, one goes northwest and one that goes east toward Mundelein
We rode this trail in early Nov 2020, and liked it so much we returned two weeks later for another run. This is one of the most interesting of the suburban trails we have ridden, with a number of bridge crossings of the creek. The trail winds through various Forest Preserve forests and meadows on its north end, before veering due south at Glenwood for a long straight stretch, then wanders through several pleasant neighborhood-adjacent parks before ending at Sauk Lake.
Well worth adding the very peaceful and scenic Black Trail loop around Sauk Lake, just be prepared for that one steep hill at the back, lol! An added benefit is that Thorn Creek Trail is amazingly smooth, with very few of those root-bump cracks that you always seem to feel so much more on the return trip.
Ignore the nonsense in the "Parking and Trail Access" section about the northern trailhead being at "Wapum" (Actually Wampum) Lake Woods. There's no trailhead there, they need to change that. Park at Lansing Woods on 186th just east of Torrence.
I am thrilled to share that the worst part of this trail mentioned in several reviews here has been freshly repaved as of November 2020 (from Route 30 all the way north to Colfax Street). Previously, this section was marred by huge cracks that ran across the full width of the trail every 20 yards or so. These cracks were between 1 and 2 inches wide – enough for foliage to blossom within – and were absolutely jarring to hit on a road bike. Now, this section is buttery smooth and an absolute pleasure to ride on.
This now places the worst section of this trail in Hammond north of Interstate 80/94. With the exception of the new pedestrian flyovers that cross Columbia and Calumet Avenues, the rest of Hammond's share is quite rough. Still, I enjoy completing the entirety of the trail from Downtown Hammond to Crown Point and back. When I start off in Hammond, I typically park in the visitor's lot of the Hammond Police Department off Douglas St. for some extra peace of mind with respect to my vehicle being left unattended for hours (downtown Hammond doesn't have the rosiest of reputations).
I parked just north of Golf at 294 right over the train tracks. Took the trail north and I loved it. The tracks do separate the trail and I’m surprised it’s not connected. The people who make and maintain these trails are national heroes. The dirt road north is perfect for mountain bikes. I rode about 7 miles to highway 68 I think it is. Awesome.
Agree with all the posters below: this is a great trail and another example of what gems these FPD trails are! So close to urban, highway, and residential, yet a secluded ride in the woods.
If riding south and west, park at the Red trailhead at Lansing Woods, just east of Torrance on 183rd Street. Late season and winter, mind the wind direction before choosing which way to ride this trail, as much of it runs due south.
11.8 miles to the end of the red trail, then you can tack on 4 miles on the black loop. 11.0 miles to the east end of the Old Plank Road trail.
I went on a walk/roll with my husband on this beautiful trail. The Fall colors were enchanting. He was able to get my wheelchair through the path without a problem. I love the wooded pathway and all of the beautiful trees and scenery.
This well maintained trail connects the Rock Run Greenway Trail to the I & M Canal Trail. The trail passes through a quiet suburban area on the north and through a more wooded and somewhat industrial area on the south.
Particularly to the north the wide trail accommodates side by side riding easily.
Overall a nice addition to the two above mentioned trails albeit too many busy streets to cross for 5 stars.
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