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 98 trails covering 1035 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 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...
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 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 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 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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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...
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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...
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 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...
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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...
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 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 North Shore Bike Path runs for nearly 8 miles between Lake Bluff and Mundelein, paralleling State Route 176 for the path's entire length. The trail is one of dozens in the Chicagoland area, all of...
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 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 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...
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 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 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 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...
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 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...
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...
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 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 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...
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...
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...
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 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 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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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 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 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 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 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 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...
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 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....
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 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 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 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 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 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...
The Thorn Creek Trail offers a paved 17-mile route traversing woodlands abundant with wildlife through several communities on the southern outskirts of Chicago. The trail travels from Brownwell Woods...
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 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...
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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....
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 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...
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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 North Shore Bike Path runs for nearly 8 miles between Lake Bluff and Mundelein, paralleling State Route 176 for the path's entire length. The trail is one of dozens in the Chicagoland area, all of...
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 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 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 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 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...
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?
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."
This trail can be described with one word...WOW!!! As construction nears completion (mostly landscaping) and pedestrian traffic moves onto the pedestrian path there is little to criticize. Awesome views of downtown Chicago and all the amenities of the lakefront make this trail a must do if you're in Chicago! I have only rode from Promontory Point to North Avenue Beach but look forward to riding the trail completely in the near future. Access to Grant Park, Millenium Park, Buckingham Fountain, Chicago River Walk, Northerly Island, Soldier Field, Museum of Science and Industry, Field Museum, Shedd Aquarium, Adler Planetarium, and Navy Pier plus numerous beaches along the route. Peak days and times will make the trail busy but there is much to enjoy all around you as you make your way through the hustle and bustle of Chicago and it's magnificent lake front views!
I've had the opportunity to ride this trail several times now, and it's always a great ride. It's hard to describe the feeling of being on your bike, looking to the west and seeing the Chicago skyline; turning to look East and seeing Lake Michigan, the beaches, the people, the boats, yachts, ships.... It's fantastic.
Along the way in summer there are fun places to stop for a meal, a snack, a beer or glass of wine... and listen to some relaxing (live) music. There are several beaches along the ride, each with their own "flavor". We ride at a leisurely pace, and spend the greater part of the day on the trail. We ended our ride on one occasion with a late night dinner at Millennium Park - what a treat it was dining al fresco while hearing live music playing at the music festival a level up from the restaurant.
The only negative was navigating some congestion at Navy Pier, but that was relatively short-lived, and I believe it should be less of a hassle now that the nearby road/bridge construction is complete. The trail is paved and in good condition, however it's best to come with the expectation that this is a ride meant to be enjoyed at a slower pace. On a nice day there are many walkers, bikers, roller bladers, all of which I found fascinating, and rolling with it, rather than fighting it, is the way to go. There's so much to see and take in!
Riding this trail is fantastic - the city, the lake, the diverse and interesting people enjoying the best summer offers is truly a treat.
This is an amazing trail in the city I love. It’ll take you north to Hollywood st and south to the south short cultural center. North you can continue on the streets until hooking up with more trails all the way to WI. South is the same all the way to Indiana. But... ...it’s currently under construction. They’re separating the bike path from the runner/walking path so the trail is being worked on now. When it’s finished it will be magnificent. Just wanted to give you a heads up!
If you start in Algonquin I suggest parking in the park at the corner of Rt. 62 and Main St. I parked near the clock tower and had to ask a passing cyclist where to catch the trail. Once on the trail, the portion from Algonquin to Elgin is one of the best marked trails I've been on. It is very well maintained and passes through historic areas and scenic beauty. There were many walkers and joggers as well as cyclists. Also, there are plenty of quality rest areas along the way.
Have photographed 30 deer since walking from Dam No 4 Woods to Campground Road Woods, a nice relaxing walk to see squirrels, chipmunks, birds, rabbits and o yes the deer. This is a beautiful trail to walk and much safer than walking on the street or road. I live one mile from Dam No 4 Woods so it is easy for me to get there.
Solid 17 mile path for a decent workout. Fairly flat and well maintained. Follows highway IL 64 for the most part but does veer away in certain parts. Country and town mixed together. Excellent ride for the recreational biker who wants to get away but not to far away from civilization for a couple hours. Started and ended in Sycamore so there are easy amenities before and after the ride.
Set out on a gorgeous fall day and enjoyed the scenery, but not for very long. I had a road bike and spent most of the first six miles east from Elkhorn watching the trail surface. It was pretty well maintained but the 'concrete' only applies to the road crossings. The rest is somewhat crushed gravel. And then just past the coffee shop (about mile six) it gets sandy and very large gravel and I had to turn around. The good news is that the roads are excellent out here, so I rode back on those. Passed almost no other trail users and the tree canopy is lovely. Would like to ride this again but definitely suggest you take a hybrid bike!
Great Sept evening spin, goldenrod, milkweed,rattlesnake master...
But to pause in pedalling made us mosquito fodder. Don't forget repellant!
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