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 103 trails covering 4726 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 DuPage River Trail spans over 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 and...
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...
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...
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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...
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 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 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 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...
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...
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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...
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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 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...
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...
Prospect Heights has very few sidewalks, so biking, inline skating or walking are moved to the streets or in the parks. Don't underestimate the Prospect Heights Bike Path which is over four miles of...
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 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 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 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 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...
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 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 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 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 Cal-Sag Trail (or, Calumet-Sag Trail) is currently under active construction. It currently has a competed section of over 15 miles, stretching from near its western terminus at the John Husar I&M...
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 Oswego Prairie Trail is a short paved route that occupies an overhead electric utility corridor owned by Commonwealth Edison. The path forms a direct link between two parks in Oswego—Farmington...
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 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 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 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...
The Joliet Junction Trail is a paved path that travels north–south through the west side of Joliet. It occupies an abandoned Elgin, Joliet and Eastern Railway corridor that in its last years was known...
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 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 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 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...
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...
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...
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 Fort Hill Bike Path trail sits on the north side of Peterson Road/ County Road 20. The trail peels away from the Prairie Crossing Bike Path at Midlothian Road and extends west, passing industries...
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 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 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 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 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 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 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...
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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 DuPage River Trail spans over 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 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...
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 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 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,...
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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...
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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 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...
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 Kankakee River Trail is fairly wooded and runs primarily through Kankakee River State Park. Walkers, bicyclists, and cross-country skiers can enjoy more than ten miles of trail along the north...
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...
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...
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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...
So happy to have this nearby. Lots of things to enjoy along this trail when you're in the main part of the park.
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.
This trail is nice to walk to the store or just to enjoy the day. Its a short trail along the road. I think its mostly used for the people that live along it.
The red path is a 7 1/2 mile loop around Busse Woods. It is my personal go-to for a quick bike ride. The path is very well maintained with a great mix of wooded areas and open areas. The bridges over the Higgins Road mean no stopping for heavy traffic. The only downside is that the trail gets very crowded at peak times.
If you are in the Chicago suburbs and love long bike rides, this trail is a must. Not crowded at all, very few roads to cross, and fairly well maintained. The hills are practically non-existent, but frankly, that's perfectly fine. I have nothing bad to say about this trail.
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