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 81 trails covering 913 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 Dunes Kankakee Trail is a 3-mile walking and bike path that begins in the Indiana Dunes State Park and travels south to Chesterton. It connects the Calumet Trail, which is also in the state park,...
The Northerly Island Trail offers access to a vast, natural oasis in one of the largest cities in America. Chicago’s Northerly Island—actually a 91-acre peninsula—was designed by Daniel H. Burnham,...
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...
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 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....
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 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 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...
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 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 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 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...
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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 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 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 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 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...
The Marquette Trail offers picturesque views of Lake Michigan as it travels through the Indiana Dunes National Lakeshore. This scenic route follows an abandoned rail line through a variety of diverse...
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...
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 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 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 Cal-Sag Trail (or, Calumet-Sag Trail) is currently under active construction. As of early 2018, it has a competed section of about 13 miles, stretching from near its western terminus at the John...
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The Skokie Valley Trail in Cook County parallels active train tracks in the Village of Skokie, providing easy access to both the Oakton–Skokie and Dempster–Skokie stations on the CTA’s Yellow Line....
The Dunes Kankakee Trail is a 3-mile walking and bike path that begins in the Indiana Dunes State Park and travels south to Chesterton. It connects the Calumet Trail, which is also in the state park,...
The Pennsy Greenway is currently open in three segments between Calumet City, Illinois, and Schererville, Indiana. The northern portion begins at the southern end of the Burnham Greenway in Calumet...
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 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 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...
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 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 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...
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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...
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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...
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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 Northerly Island Trail offers access to a vast, natural oasis in one of the largest cities in America. Chicago’s Northerly Island—actually a 91-acre peninsula—was designed by Daniel H. Burnham,...
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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...
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 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 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...
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 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 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 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...
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 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 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 Pennsy Greenway is currently open in three segments between Calumet City, Illinois, and Schererville, Indiana. The northern portion begins at the southern end of the Burnham Greenway in Calumet...
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 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 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 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...
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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...
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...
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...
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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...
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 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...
Have to cross busy streets on this trail, but otherwise very nice for walking or riding a bike.
Too many damn trees and straight always. No trail markings. Started at essington/ingles and ended up by the starved rock dam...
Took a early spring hike and path is wide and very easy to navigate. An occasional bench to sit, watch and reflect. Birds were everywhere. Some sightings were red headed woodpeckers, flicker woodpeckers, blue birds, blue jays, sand hill cranes, killdeer,,brown creeper, numerous red wing black birds and robins and many more birds I can’t name. Enjoyed taking the grassy trails that took us closer to water. A delightful place to visit!
We have been riding this trail every weekend for 10+ years. However, we took our first ride of the year for 2019 yesterday, and the trail is in bad shape. With the bridge out, there is no way to get on the Centennial Trail from Willow Springs. Is there a plan to repave the trail anytime soon?
I rode this trail yesterday while I had some time to myself. It was in the 30's, with a very light snow falling. That meant that very few people were out on the trail. That also meant it was a great day for a ride. I parked off of Golf Road next to the Black trail, rode south and did two loops on the red trail before returning to the car. The whole ride came to a bit over 17 miles. I probably saw as many animals as people. Three deer were grazing next to the trail, there were a couple of elk out in their fenced in area, and, most concerning, was coming around a corner and hearing an animal noise only to look over and see a skunk poised to spray me! Fortunately I was going past it, not at it, so I came away clean. Probably due to the lack of sun and my unfamiliarity with the Preserve, I never seemed to have a good sense of what direction I was riding. There were plenty of maps, but I just didn't get a feel for it. The environment varied quite a bit from prairie to forest. There had been a recent controlled burn, primarily in the woods, so there was a light smell of fire still in the air. It's definitely a great trail to ride when the people count is low!
The bridge crossing the Des Plaines River at the east end of the trail (Columbia Woods) is still closed. It was originally scheduled to be finished in October of 2018. Here is an update from IDOT:
"The bridge replacement over Des Plaines River in Willow Springs at Columbia Woods started in early summer 2018 and will be completed in late spring 2019. The project was initially delayed due to higher than normal water levels on the Des Plaines River which impacted reconstruction efforts. Also parts of the project were re-designed which effected the overall project timeline. Thank you for your patience."
This trail can be described with one word...WOW!!! As construction nears completion (mostly landscaping) and pedestrian traffic moves onto the pedestrian path there is little to criticize. Awesome views of downtown Chicago and all the amenities of the lakefront make this trail a must do if you're in Chicago! I have only rode from Promontory Point to North Avenue Beach but look forward to riding the trail completely in the near future. Access to Grant Park, Millenium Park, Buckingham Fountain, Chicago River Walk, Northerly Island, Soldier Field, Museum of Science and Industry, Field Museum, Shedd Aquarium, Adler Planetarium, and Navy Pier plus numerous beaches along the route. Peak days and times will make the trail busy but there is much to enjoy all around you as you make your way through the hustle and bustle of Chicago and it's magnificent lake front views!
I rode the trail December 15, 2018 and it was very difficult!! Lots of very loose rock, shrubs across trail, etc.
I've had the opportunity to ride this trail several times now, and it's always a great ride. It's hard to describe the feeling of being on your bike, looking to the west and seeing the Chicago skyline; turning to look East and seeing Lake Michigan, the beaches, the people, the boats, yachts, ships.... It's fantastic.
Along the way in summer there are fun places to stop for a meal, a snack, a beer or glass of wine... and listen to some relaxing (live) music. There are several beaches along the ride, each with their own "flavor". We ride at a leisurely pace, and spend the greater part of the day on the trail. We ended our ride on one occasion with a late night dinner at Millennium Park - what a treat it was dining al fresco while hearing live music playing at the music festival a level up from the restaurant.
The only negative was navigating some congestion at Navy Pier, but that was relatively short-lived, and I believe it should be less of a hassle now that the nearby road/bridge construction is complete. The trail is paved and in good condition, however it's best to come with the expectation that this is a ride meant to be enjoyed at a slower pace. On a nice day there are many walkers, bikers, roller bladers, all of which I found fascinating, and rolling with it, rather than fighting it, is the way to go. There's so much to see and take in!
Riding this trail is fantastic - the city, the lake, the diverse and interesting people enjoying the best summer offers is truly a treat.
This is an amazing trail in the city I love. It’ll take you north to Hollywood st and south to the south short cultural center. North you can continue on the streets until hooking up with more trails all the way to WI. South is the same all the way to Indiana. But... ...it’s currently under construction. They’re separating the bike path from the runner/walking path so the trail is being worked on now. When it’s finished it will be magnificent. Just wanted to give you a heads up!
If you start in Algonquin I suggest parking in the park at the corner of Rt. 62 and Main St. I parked near the clock tower and had to ask a passing cyclist where to catch the trail. Once on the trail, the portion from Algonquin to Elgin is one of the best marked trails I've been on. It is very well maintained and passes through historic areas and scenic beauty. There were many walkers and joggers as well as cyclists. Also, there are plenty of quality rest areas along the way.
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