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 122 trails covering 4865 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.
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 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...
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 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 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 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 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 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...
Lake Arlington is an artificial lake and popular recreation area in Arlington Heights in Cook County. The park features amenities to interest visitors of all ages and it is a local favorite for family...
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 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....
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...
Note: This developing route is not yet fully contiguous – it is just over 50% complete. Please refer to the Trail Map for more information on the existing sections of trail, as well as the online...
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 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 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...
This shared-use path runs east-west through the village of Carol Stream in Du Page county. Sitting on the grassy north side of Lies Road between Fair Oaks Road and Gary Avenue, the path is used as an...
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 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...
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 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 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 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 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...
The Fort Beggs Bike Trail (North) is a nearly mile-and-a-half long trail in Plainfield, Illinois. The trail shares the electric utility right-of-way, stretching from Fort Beggs Drive south to Spring...
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 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 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 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 Lily Cache Greenway travels east-west across Bollingbrook, from the ComEd Greenway to the Plainfield border. The trail more or less follows the course of its namesake creek, and is characterized...
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 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....
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,...
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 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 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 Great Divide Trail sits is a one mile non-motorized trail through a negihborhood at the northern tip of Joliet, Illinois. The paved trail, which sits in the shadow of electric transmission lines,...
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 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 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 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...
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 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 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 ComEd Greenway is an asphalt multiuse pathway running north-south through the village of Bollingbrook. The trail's name is an abbreviation of Commonwealth Edison, the name of the electric utility...
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 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 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 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 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 2.3-mile multiuse trail wraps around Lake Andrea in Pleasant Springs Park. The trail is an easy walk, run or ride around the lake, and is accessible for a wide range of users. It also helps users...
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 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...
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 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 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...
Running between the suburbs of Chicago Heights and Joliet, the Old Plank Road Trail offers views of oak trees and sugar maples, prairie grasses, and wildflowers that peek up 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...
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...
I park at the trailhead just over the border on Russel Rd. I frequent this trail because it's only 10 min. from my home. I enjoy riding through marshland and near the river to see the diverse foliage and wildlife. This trail does undulate a bit so your legs and gears are gonna get a workout. (but not too bad) This trail gives me the opportunity to ride pretty much as long or short a distance I wish. Some of the crushed gravel does get soft in spots, but I do believe it from when it floods on certain occasions. The trail does provide a few restrooms along the way. i do recommend this trail to anyone. Thanks.
I parked at the trailhead off of Keystone and was happily surprised there were toilets available. I had driven nearly an hour from Kenosha. The trail West started with a slight gradient, but nothing steep. The trail enters into what I would call a corridor of trees almost giving me the feeling of a tunnel. Gorgeous ride on crushed gravel. About 3 miles in you come to the end, BUT, if you take the road south just over the tracks and a quick right, you can pick the trail back up to completion at around 5.7 miles. From red barns to an overlook of water, this trail was spot on! I rode back past the parking lot to get to the Prairie Trail. Get ready for a nice hill to climb! (WHEW!) It is a 1.5 mile ride east to the Prairie Trail from the parking lot. I was simply amazed how nice this little jem of a trail is down here in Hebron. Thanks!
We've ridden the Great Western trail from St. Charles to Sycamore and back a bunch of times. It became one of our favorite rides during the pandemic because it is much less crowded than the trails in the more densely populated parts of the Chicago area. It's pretty straight and reasonably flat. There are a reasonable number of trail users near the St. Charles trail head but the trail is never crowded and the Sycamore end of the trail is pretty deserted. The scenery is more agricultural than wild but it's nice nevertheless. The trail surface is a mix of asphalt and gravel and is in pretty good shape. If you follow the trail towards Sycamore from the Great Western trailhead there is a park with tables, benches and a restroom which is where we usually take a break before returning to St. Charles.
I recently rode the Prairie Trail as part of a ride from Geneva, IL to Lake Geneva, WI. It is a beautiful trail and definitely rideable on a road bike if the path is dry (I had 28mm tires). It’s crushed limestone for ~8 miles from Ringwood, IL to Genoa City, WI — exactly like the Illinois Prairie Path or Great Western Trail. Like the description says- only the northernmost 1/4 mile between the Hebron Trail and Genoa City is chunkier gravel.
Thanks everyone for your previous reviews!
I recently rode the Prairie Trail as part of a ride from Geneva, IL to Lake Geneva, WI. It is a beautiful trail and definitely rideable on a road bike if the path is dry (I had 28mm tires). It’s crushed limestone for ~8 miles from Ringwood, IL to Genoa City, WI — exactly like the Illinois Prairie Path or Great Western Trail. Like the description says- only the northernmost 1/4 mile between the Hebron Trail and Genoa City is chunkier gravel.
Thanks everyone for your previous reviews!
Great path. Some of the roads within Fermilab that used to be accessible are now off limits, so stay on the trail!
This was the first day I rode this trail. 19.1 miles in 1 hour and 22 minutes. Really nice!
Good trail to walk but because of 355, it’s not a very peaceful walk.
Great walking trail to the store. Or just a short nice day walk.
This trail is nice to walk on Maybe to go to the store or just enjoy the day it's a short trail it's mostly used by I think the people that live right next to it . the trail is along the road.
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