Explore the best rated trails in Crestwood, 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 965 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 Thorn Creek Trail offers a paved route traversing woodlands abundant with wildlife through several communities on the southern outskirts of Chicago. The trail travels from Brownwell Woods in...
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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...
Prairies and dunes are just two of the natural features you’ll experience on the Prairie Duneland Trail, located just a few miles south of the Lake Michigan shoreline and the Indiana Dunes National...
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...
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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...
The North Branch Riverwalk is a 0.6 mile biking and walking trail located on Chicago's northside along the North Branch of the Chicago River, nestled between Gordon Tech High School and Lane Tech High...
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...
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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 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 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 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 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....
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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 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 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 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 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...
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 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 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 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 Vale Park West Pathway is a multiuse trail in the Chicago suburb of Valparaiso. At 0.7 mile long, the trail passes through a mix of woodland and prairie, as well as over a creek on a 220-foot...
Prairies and dunes are just two of the natural features you’ll experience on the Prairie Duneland Trail, located just a few miles south of the Lake Michigan shoreline and the Indiana Dunes National...
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 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 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...
Note: Erosion caused by surging waves off Lake Michigan has caused the trail to collapse in sections. The eastern half of the trail along Lake Michigan is closed indefinitely. See the Chicago Park...
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 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 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 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...
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...
The Burnham Greenway is composed of two distinct portions that both run along a former railroad corridor between Chicago and Lansing, Illinois. There are plans to extend and connect these short...
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,...
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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 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 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 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 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...
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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,...
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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 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 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...
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 North Branch Riverwalk is a 0.6 mile biking and walking trail located on Chicago's northside along the North Branch of the Chicago River, nestled between Gordon Tech High School and Lane Tech High...
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,...
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...
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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 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 Burnham Greenway is composed of two distinct portions that both run along a former railroad corridor between Chicago and Lansing, Illinois. There are plans to extend and connect these short...
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 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...
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...
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 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...
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 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...
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 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 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...
I've been riding this trail since the early 90s and absolutely adore it. In high school I would ride from St Charles to Batavia and back every morning, and now I love doing 50 mile round trips from Oswego up to St Charles.
Absolutely scenic any time of year. As some have mentioned it can get busy on summer weekends, but nothing too bad. 99% of it is paved so road bikes should have no problems at all.
Tons of parks to take breaks at, lots of great restaurants and food stops as well. The trolley museum in Elgin, the Fabyan museum, Japanese tea garden, and windmill in Batavia are must-stops.
The FRT also links up to the Virgil Gilman Trail, the Prairie Path (one of its spurs), and quite a few others, so if you're really looking to rack up the milage you have a lot to choose from!
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.
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.
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.
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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