Find the top rated trails in Crestwood, whether you're looking an easy walking path or a long bike trail, you'll find what you're looking for. Click on a 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,...
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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 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 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 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...
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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 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 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 4.4-mile River Bend Trail is so named for the loop of Fox River along which it follows on its eastern end. It's here that you can connect to the scenic Fox River Trail to travel 43 miles along the...
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 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...
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 Erie Lackawanna Trail rolls nearly 18 miles between Crown Point and Hammond, two former rail junctions whose early fortunes were tied to the tracks carrying people and goods to and from Chicago....
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 Old Plank Road Trail travels nearly 22 miles between Chicago Heights and Joliet across a densely populated suburban landscape, where you’re never far from a café or espresso stand. Still, you...
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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...
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...
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...
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...
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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 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 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 North Branch Trail follows the North Branch of the Chicago River nearly 20 miles through Cook County. The trail was originally a dirt path often used for horseback riding; though it’s now paved,...
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 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 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...
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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 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,...
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 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 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...
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...
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...
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 Bike Path runs between Woodland Trails Park and Country Garden Park, paralleling the commuter rail tracks on its north–south leg. The trail provides a nice off-road route through 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 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 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...
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 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...
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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 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 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 Illinois and Michigan Canal State Trail follows the eponymous waterway alongside the Illinois River. The trail runs along the old canal towpath from LaSalle to the historical quarry town of...
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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 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 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...
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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....
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...
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 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 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 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 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 Iron Horse Heritage Trail in Portage, Indiana, runs for 5 miles between Max Mochal Road (SR 149) at the east end and County Line Road near US 20 at the west end. The trail passes through a...
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The Veterans Memorial Bikeway begins in Hebron in northwestern Indiana’s Porter County. From there, it follows the diagonal route of the former Pennsylvania Railroad for just over 8 miles through Lake...
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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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 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...
I finally completed the trail in LaSalle last weekend, I had been completing the entire route in segments throughout the summer. Overall, I enjoyed the experience, I liked the historical placards and informative mile markers. Yes, I stopped and read every one of them! I thought it was really well done, and very interesting history of the canal and its construction and usage. Cool grande finale ending up in LaSalle where the packet boat and mule towpath was in full display with the tour.
I started in Lemont where the trail begins, through Lockport (the old canal headquarters) and got through Joliet. A must see is the old Joliet Iron Works, an interesting historical walking tour. The next segment I completed was from Joliet (Rockdale) to Channahon, with beautiful views of the Illinois River. Saw an abundance of varied wildlife as the canal here is wide with plenty of water still left in it. McKinley Woods Park is a nice diversion to take a break. Channahon to Morris was the next segment, again with nice views of barges on the river and the Dresden dam area. From Morris to Marseilles the trail begins to get more woodsy, and at some points the trail goes from crushed limestone to single track dirt. This is where the canal is hard to see, as it has dried up over the years, thus there is less wildlife to see. From Marseilles to Ottawa the trail is still woodsy, but becomes more industrial as you are riding next to train tracks and grain silos along the river for much of it. Ottawa to Utica becomes more scenic as you start to see the St Peters sandstone cliffs at certain points. Finally from Utica to LaSalle you can see much more of this, and the trail ends with a lock with all of its functioning parts, as would have existed back in the day.
I normally ride on much more challenging, tougher and more hilly terrain with my trail bike, so this was a change of pace for me. The trail is in decent shape, but you can tell that it has not been maintained for awhile. There are bridges out in several spots (easy to get around), and fallen trees that you need to lift your bike over. All in all, I would recommend it to the casual rider, seeking an interesting history of the canal from back in the nineteenth century. Happy riding!
The trail is mostly well paved. There's a section where somebody highlighted the pavement problems in yellow paint. Not sure if they mean to fix it or just warn. It is pretty flat and does cross several roads, but nothing too difficult (mid-day at least). Bridge at Palatine is nice. I did not notice buzzing from the power towers but at the ComEd station there was some. Did not seem like it was 4 miles long, but maybe that just means it was a pleasant ride. Probably not for the speedsters, but for senior citizens, very nice. Not obvious where it starts from the parking - go east toward Wolf Road, runs along is to start.
I've now ridden the northern 20 or so miles twice, starting at Russell Road both times. The first couple miles are pretty rough due to the horses. That's not a knock on people riding horses on the trail, just the reality of hoofs digging into the crushed limestone surface. It seems to smooth out quite nicely after that and is very pleasant. Not many road crossings, which is great. Yesterday's ride was much cooler than my previous, but there are plenty of places to stop in the shade if needed. I'm not a fan of the crushed limestone surface simply because it leaves my bike caked in dust, but this is a nice trail for a day's use.
Pros:
-Relatively flat, a few minor crossings, and thankfully a bridge over Palatine Rd.
-Nice untouched easement with the electric lines overhead, some grassland restoration
-Usually not crowded
-Connection to Lake Arlington at the northwest terminus
Neutral:
-Very straight
Cons:
-You will constantly hear the power lines overhead
-You sort of ride five feet off of some people's backyards
-Southern terminus ends abruptly in a bad spot
I really wish the southern end connected to something like the Des Plaines River Trail or continued along the easement to High Ridge Knolls (a E-W easement trail) so you had some type of loop. Depending on your way home you may have to face a really messy crossing at Rand. I usually head South across Euclid and cut through the large industrial park where there is a protected pedestrian crossing across Rand.
Pros:
-After Dundee, no unsafe crossings (to my knowledge)
-Varied scenery ranging from swamp, light and dense forest, restored prairies, and old farmland
-Pretty empty on most days (south of Milwaukee can see more traffic)
-Can sporadically see larger animals (deer, raccoons, skunks, turtles, snakes). Guaranteed to see some warblers, woodpeckers, hawks, and finches when in season
Neutral
-Some areas are pretty desolate. The solitude can be nice, but I can imagine it attracts criminals.
-The gravel/packed dirt is OK for the most part. Around Lincolnshire you start seeing more asphalt.
Cons
-South of Milwaukee trail is muddy and swamp-like, very narrow paths
-Underpasses can close as can parking lots (I once drove from Milwaukee Ave. to Beck Lake without finding an open lot)
-Can be a bit confusing especially south of Milwaukee
To sum up, start north at Milwaukee. There's a big lot but you have to cross unprotected and bike beyond a hotel before the trail picks up again. After this there is only one other crossing at Dundee. Some people start across Dundee so they don't have to cross at all.
I was also surprised by the abundance of old ruins sometimes right along the trail. There's an old POW Camp, tons of old farm remains, and scattered agricultural machinery,
My husband and I wanted to take a different trail this weekend. Overall, the trail was in great shape just a couple of soft spots. It was a very hot day so we had the trail basically to ourselves. We had trouble finding the trail head in Joliet but really enjoyed a picnic lunch at the Kankakee river park.
I don't know how anyone could rate this anything but 5 stars. There are sections of this trail (Channahon to Ottawa) that are absolutely breathtaking - especially on a warm fall day when the leaves are turning color. There are long sections of the trail where you are riding between two bodies of water and it is absolutely spectacular. Access the train in Channahon and ride northeast toward Ottawa. You will not regret it!
I frequently take the VL Gilman from the access off Terry St. on the west side of Aurora and go west to Bliss Road and exit to ride the country roads west of Route 47. The Gilman Trail is beautiful and many sections are recently paved (within West Aurora) sections.
I see a lot of five star reviews and I am guessing those come from people at the north end of this long trail. South of where it crosses Milwaukee Avenue, there are some pretty poor areas. It floods out, there are unsafe road crossings. In one place it comes down to a worn path barely a tire's width. South of Touhy Avenue the surface is uneven with some rocks and old broken asphalt. I ride this trail often because it is the one closest to me, but for the stretch I know, I cannot give this a high rating. The North Branch Trail is much better, a few miles east.
We rode the section from Pottawatomie Park in St. Charles to Aurora on Saturday September 16th in the afternoon. Once we found the trail from the parking lot, it was a lovely ride and not a lot of hills. It passes through a few congested areas near parks and through downtown St. Charles but largely it was not overpopulated. There are a few places that it wasn't terribly clear which way to go, there's a main trail with trails that go off it and at one point there are two trails, one on each side of the river. Once we got to Aurora there was a bit of street riding, well marked, and then there was nothing although I knew we couldn't be at the end based on the map. The trail is all asphalt and in pretty good condition. The scenery is beautiful and goes through some nice towns.
Sunday Sept. 17th we rode the part from Norris Woods in St. Charles to the 5 or 6 mile mark which is north of Elgin. There were lots of places that were not marked well at all, there were a lot of confused riders including us. There's currently one section that is closed, we figured it out going north, going south we missed the turnoff but were able to figure out how to get back on the street. The scenery was not as nice as the south section. There are more hills on this route including one right at Norris Woods, one in Elgin that I had to get off and walk and one mid way that was very challenging. Mostly asphalt, some street riding, a couple small crushed limestone sections.
I started at Custer Park, where there is a small lot for parking. I rode the entire trail on 12SEP17 starting at 7:30 am. I didn't see anyone the first ten miles, but later in the day, I came across fellow bikers as well as runners and hikers. The trail is well kept and mostly shaded. Only about 2 miles of it is paved, the rest is crushed limestone. Although I was riding my mountain bike, it has a thin smooth tread 'commuter' tire on the front. I had zero problems with the trail surface. In fact, I'm fairly certain I could use my road bike on the trail, but I'm not going to risk it. There are benches at irregular intervals for breaks, restrooms, and a couple water fountains. Overall it was a great ride and I'm looking forward to doing it again.
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