Explore the best rated trails in Highland Park, IL. Whether you're looking for an easy walking trail or a bike trail like the Illinois & Michigan Canal State Trail and ComEd Greenway. With more than 120 trails covering 4975 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 Bull Valley Road Shared-Use Path travels along the south side of Bull Valley Road in the city of McHenry, Illinois. The paved path is suitable for non-motorized uses including walking, jogging,...
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 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 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 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...
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 Marquette Trail is part of the Marquette Greenway, which will one day span more than 50 miles through Northwest Indiana, connecting communities along the southern shore of Lake Michigan. The...
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 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 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 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 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 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 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 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 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,...
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...
Lake Renwick Preserve is home to an artificial lake of the same name that was created from former quarries where aggregates for concrete were once mined. Today, the lake is a recreational amenity in...
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 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 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...
The Bull Valley Road Shared-Use Path travels along the south side of Bull Valley Road in the city of McHenry, Illinois. The paved path is suitable for non-motorized uses including walking, jogging,...
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 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 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 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 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 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...
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 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 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 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 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 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 Hebron Trail rolls across the northern Illinois prairie through the former corridor of the Kenosha and Rockford Railroad, known as the Kenosha Division Line at the time of its demise in 1939....
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...
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...
This bike path sits on the east side of Almond Road between Washington Street and Fairfield Lane in Gurnee. The 8-foot wide asphalt path is used by residents as a spot for exercise and recreation, but...
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 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 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...
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 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...
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 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 Oak Leaf Trail is the jewel in the crown of Milwaukee County’s extensive trail system. The trail meanders for more than 125 miles in and around the city of Milwaukee on a changing terrain of flat...
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 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...
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 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...
With farmland to the east and the Des Plaines River Floodplain to the west, this picturesque trail is a relaxing adventure on two feet or on wheels. The crushed stone trail runs from Prairie Springs...
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...
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 KR Trail is a new addition to Kenosha County’s growing bike-ped network. The trail picks up where the Kenosha County Bike Trail leaves off, in Petrifying Springs Park. From the northwest corner of...
The Stone Mill Trail runs between Lawrence Road in Harvard and Maxon Road in Chemung. The 1.5-mile, paved trail mostly parallels County Highway 17 (Ramer Road) and active railroad tracks, and will...
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...
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 Long Prairie Trail journeys across the width of agricultural Boone County for nearly 14 miles on the railroad corridor previously used by the Kenosha and Rockford Railroad, later known as the...
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 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...
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!
Very rough on the bike. There are more bumps than smooth asphalt. Not a smooth ride. Would be nice if they fixed it. I wouldn't ride this again.
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.
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