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 101 trails covering 4713 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.
_183583_st.jpg)
_176080_st.jpg)
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 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 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 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 Struckman Boulevard Path is just over a mile long, stretching between Bartlett Road and State Route 59, (although the path narrows from the end of Sunset Park up to the end on SR 59). That said,...
Closure Notice: As of April 2021, the portion of the bike path on the Route 176 bridge over the Des Plaines River is closed for bridge repairs. Trail users can follow posted detour signage via the Des...
_194062_sc.jpg)
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....
_179560_sc.jpg)
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 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 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...
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...
_172068_sc.jpg)
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...
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...
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...
_111257_sc.jpg)
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...
Little Calumet River Levee Trail stretches from Munster to Gary, Indiana. The trail zigs and zags through a number of local parks including Riverside Park, Wicker Memorial Park, Homestead Park,...
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 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...
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...
_176080_sc.jpg)
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...
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 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 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 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 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 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...
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,...
Little Calumet River Levee Trail stretches from Munster to Gary, Indiana. The trail zigs and zags through a number of local parks including Riverside Park, Wicker Memorial Park, Homestead Park,...
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 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 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 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...
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 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 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...
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 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 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 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 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...
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...
_191267_sc.jpg)
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 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 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 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 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 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...
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 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...
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...
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 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 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 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...
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...
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...
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 Grove Road Trail parallels the local thoroughfare in the Village of Oswego, located near the southwestern edge of the Chicagoland metropolitan area. In the north, the trail begins on the east...
The Marquette Trail, also known as the Marquette Greenway, will one day span more than 50 miles through Northwest Indiana, connecting communities along the southern shore of Lake Michigan. The...
What an amazing experience Hope and I had! Was able to jump off the trail and be hosted at a nearby barn mid-way back to homebase (my Barn in Carol Stream) located ON the path. Awesome scenery rolling by and big thank you to the cyclists who were so kind to my horses as they went on their merry way. I recommend this to anyone. My horse wears a diaper bag to take care of any piles for consideration of other users. Truly a joyful experience that took two days travel. This is the second time I have done this by horse. The portion from Carol Stream to Villa park is equally horse friendly (I did that stretch under saddle) and is one days ride there and back to my home base. I can't thank the RTT enough for this amazing system in our area that makes horse travel amazing and feel like I'm in the middle of serenity...with urban amenities close at hand. http://buffalomoonexpedition.blogspot.com. Tomorrow we continue up to South Elgin and I'll be back to review that section when we complete it in about another 4 days travel time.
I started in Wheaton and rode to South Elgin, and it turned out to be the longest bike ride I have ever taken at 14.4 miles one way! It is a very easy ride and the elevation changes are for the most part subtle. The trail itself is by my standard very well maintained, and it was nice to ride on around 3 miles of paved trail after crossing Stearns/ Route 25. If you like to be alone, there are long LONG stretches of just you and the path. With that in mind, it would be advisable to carry a bicycle pump or tire patches. Be observant of horse apples and in the Autumn, walnuts. My goodness, there is a lot walnut trees lining that path.
Perfect weather. Not crowded, but it was a Thursday. Nice trail. Will ride again.
Explored this trail, and it’s really good with lot of forest area and greenery. The paved road through the entire ride is a big plus for the trail. And the loop is a plus as well. We don’t feel like going straight and getting back.
I won’t repeat all of the good reviewers before me, but will emphasize that if you are biking the trail that you should get there early before it gets really busy. The loop makes for a good 1 hour ride and a wonderful place to take your dog, family and friends for a stroll. Enjoy!
This is a solid low pressure multi-use trail that is in good shape. It provides the rider with some Urban, Suburban, Industrial and Country scenery. There are numerous parking lots for easy access to the trail. You will enjoy riding past golf courses, wetlands, BlackBerry Farm and taking a lap around the Waubonsee Valley Community College Campus. There are a number of roads to cross on the east side of the Fox river, so heading to the West provides a more relaxing experience. The bottom line is that if you want to get away from the hustle and bustle of the River Trails to the North, throw your bikes on your rack and enjoy the fall colors on the V.L. Gilman trail!
This trail is very poorly marked. It was very difficult to find the trail when crossing streets and such. Also no signs pointing which way to go when the trail intersected with another path. Also to much of the trail is along busy streets! It’s also very short. also
I love it because i saw everything and see cool boats and it was not dirty it's so clean and beautiful i have fun and it was awesome
Nice trail and very good for a decent workout. Lots of up and down hills. Noticed a trekking path as well (need to explore next time). Deers crossing the road and the curling paths. Really good trail. ¿¿¿ Be careful in the curves though, might just be slippery if you are coming down without control.
09/01/2021 - Excellent trail. Beautiful September day for a ride. This is a well maintained trail perfect for road or mountain bikes. Rode from Sycamore trail head to the St. Charles ( LeRoy Oakes Forest Preserve) head and back. I can highly recommend to any biker looking for a great ride. And a special thanks to the gentleman who joined me spontaneously for part of the way. Good conversation always makes the miles go fast.
TrailLink is a free service provided by Rails-to-Trails Conservancy (a non-profit) and we need your support!
Map Search
_0_st.jpg)
_0_st.jpg)
_172068_st.jpg)
_199151_st.jpg)
_198601_st.jpg)
_177065_st.jpg)
_196059_st.jpg)
_140728_st.jpg)
_191267_st.jpg)
_144630_st.jpg)
_194062_st.jpg)
_179560_st.jpg)
_111257_st.jpg)
_0_st.jpg)
