Find the top rated trails in Winnetka, 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 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...
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 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 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 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 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 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,...
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 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 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 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 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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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 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...
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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...
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 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 Erie Lackawanna Trail rolls nearly 18 miles between Crown Point and Hammond, two former rail junctions whose early fortunes were tied to the tracks carrying people and goods to and from Chicago....
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 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 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 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 Pike River Pathway is a short trail on both sides of the reconstructed Pike River in the Village of Mount Pleasant. The path is convenient to several neighborhoods in the community. Birds, frogs...
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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 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 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...
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...
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...
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 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 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 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 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 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 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...
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...
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...
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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...
The Calumet Trail traverses the south side of the Indiana Dunes National Lakeshore, a unique ecosystem of forest, marsh, dunes and beach along Lake Michigan. This dirt and crushed limestone path...
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...
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 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 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 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 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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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 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...
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 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 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 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...
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The the Fox River Trail (FRT) was built on stretches of three former railroads: Chicago, Aurora & Elgin; Aurora, Elgin, & Fox River Electric; and Chicago & North Western. Today, it hosts a multitude...
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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,...
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 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 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...
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 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...
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,...
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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...
Nice scenic path covering 2 creeks and a small bridge. Connects to a longer path if wanting an extended ride. Definitely a few hills but nothing to taxing, especially with the tons of bench's they have directly next to the path you can take a break whenever you like. A bunch of shaded path makes it both beautiful and a great choice on a hotter day.
I had a very nice bike ride on the trail from Elkhorn to the west end of Burlington. Started at the well-marked parking lot just east of Elkhorn, the trail is relatively flat and hard-packed gravel. It passes through farm fields and rich tunnels of greenery. I enjoyed lots of colorful wildflowers and birds along the way. Even glimpsed a beaver that visited the trail near the White River bridge. The creeks and river are well marked, and there are plenty of benches to rest along the way. Took a little side trip off trail in Lyons and visited its veterans memorial at the flag pole, listing its local war heroes dating back to the Spanish-American War. There's a nice coffee shop in Springfield. I rested in its shady yard, but it's only open on weekends. Heading back from the Burlington trail head, I noticed the trail gradually goes uphill, or at least it seemed that way, as I completed the 24-mile round trip on a hot summer day.
Decided to do this trail instead of the Old Plank Trail. Much better than the long straight trail. Many winding turns, the loop through the Preserve at the end is a nice turn around spot. Signage could be a little better though.
Road the trail today and had a great experience. If part of it was once bumpy, it has been repaired. Most of the trail is new and all of it is terrific to ride. Beautiful scenery, bathrooms along the way, easy to park and get on. We rode all 10 miles and will come back again and again.
First off, this is my go-to trail and I love it. However, there are 2 areas of the trail that have been closed too long and I wonder who is responsible for making repairs.
The first is on the south side of Elgin along Raymond St where the path used to run along Poplar Creek and go under a bridge. That portion of the trail has been closed for several years now and nothing appears to be happening with regard to repairs.
Bikers are forced to proceed south on Raymond then right on Riverview Drive and go 2-3 blocks to rejoin the trail. There are no directional signs for users to follow.
The second area is near the South Elgin dam where brush and fallen branches have closed the trail making it necessary to cut across a grassy field adjacent to an industrial area in order to rejoin the trail. Again, no signs are in place to aid bikers to find their way around.
Again I ask who is responsible for repairing these areas?
I love this trail for biking! Great forest and savanna scenery. Thankfully most of it is not parallel to roads, and none of it is old train tracks, which I find more boring. Really feels like you're moving across country under your own power.
We live near the southern section of this trail, so we have rode that portion multiple times. It is a night and day difference with the northern portion. The southern end is just not very pleasant. Trail is in poor shape, poor signage and due that section of river, the area is prone to flooding. Viaducts are usually impassable, flora is mostly invasive species, lot of trash , etc etc.
The north end however (maintained by Lake Co. as opposed to Cook Co.) is just great. Well groomed, tons of signage, usable viaducts, clean, etc. This section meanders through forest, open prairie , some farmland. The scenery is beautiful, especially mid summer with the plants in full bloom.
Highly recommend sticking to north of Cook Co. We plan on finishing the entire trail a section at a time until we hit Wisconsin!
Walked the trail from Bryn Mawr to Touhy and had a excellent time. very happy to see the Touhy overpass being built and the call boxes that can summon medical help if needed are excellent to have if a person does not have a cell phone to call 911 once my bicycle is repaired I will be riding this trail from Bryn Mawr to Dempster.
Great trail to walk on once my bicycle is repaired I will be riding this trail all the way up to Skokie , nice that Sauganash Park is by the trail for use of the drinking fountain or restrooms.
The reviews are ALL about biking. This trail is sort of inline friendly but it has a lot of flotsam, sticks, debris from trees, and there are lots of repairs made with that sticky tar substance, that the skate wheels are not too good on. Some parts are pretty rough asphalt and some are fairly smooth. Bigger wheels are probably better, though they also make you faster. The street crossings are semi cut curbs with lots of bumps and broken cement to make your wheels stick, unless you're good at navigating these obstacles or good at jumping. This gets worse the further east you go on the trail. *There's a few places where the trail runs downhill (going W at Wolf Rd for one) and then spills directly into a busy street. You'd better practice your stopping skills. I think they should send a sweeper down this path at least a few times a month. I bike this trail and it's really good for that. I've skated it as well, but that was over 10 years ago when I was more confident. One bad fall with a twisted rotator cuff made me more wary since (a jogger wouldn't make way and my avoidance of her made me lose it). People walking 3 abreast and those with dogs on long leashes are also good to avoid.
Ditto on the comments about bumpy sections. The trail could use some better signage where it deviates, and could use mile markers. Also, I suggest if you start in the north, park behind the Wendy's next to the Indiana Welcome Center along I-80. Besides the south end, that's the only restroom you will find on the trail. And watch out crossing roads...seldom will drivers stop for you.
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