Find the top rated trails in Chesterton, 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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When complete, the LaSalle Trail will travel an arrow-straight 3.5 miles between Roseland Town Park in Roseland and the Indiana–Michigan state line. Michigan is currently working on building a trail...
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 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 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....
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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...
In just a few short miles, the Wauponsee Glacial Trail leaves the urban confines of Joliet to bask in open farmland and reclaimed tallgrass prairie where the bison roam again. Named for a glacial lake...
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 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....
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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 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...
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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 Monterey Erie Trail occupies the same railbanked corridor as the longer North Judson Erie Trail to its west, and the two rail-trails are planned to be linked in the future. Monterey and North...
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 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 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...
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...
Although less than 1 mile long, the West Bank Walkway offers lovely views of the St. Joseph River in downtown South Bend. Midway, a converted railroad trestle over the waterway connects trail-goers to...
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...
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 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...
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 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...
The North Judson Erie Trail occupies the railbanked right-of-way of the former JK Line Railroad, running 9 miles from downtown North Judson southeast to US 35 near Bass Lake. Eventually, the trail...
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...
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 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 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 Monterey Erie Trail occupies the same railbanked corridor as the longer North Judson Erie Trail to its west, and the two rail-trails are planned to be linked in the future. Monterey and North...
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...
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....
South Bend’s Northside Trail closely follows the east bank of the St. Joseph River from Howard Park to the western edge of Mishawaka. Along the way, you’ll have access to Viewing Park and Veterans...
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...
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...
In just a few short miles, the Wauponsee Glacial Trail leaves the urban confines of Joliet to bask in open farmland and reclaimed tallgrass prairie where the bison roam again. Named for a glacial lake...
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The northern portion of the East Bank Trail was one of the first rail-trails in Indiana, opening in 1988. The asphalt-surfaced trail stretches for about 0.5 mile through tree-lined South Bend...
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...
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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...
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 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....
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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...
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 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 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 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 North Judson Erie Trail occupies the railbanked right-of-way of the former JK Line Railroad, running 9 miles from downtown North Judson southeast to US 35 near Bass Lake. Eventually, the trail...
First-time visitors to the Oak Savannah Trail might be surprised at the profusion of natural areas they’ll encounter as they travel the 8 miles between Hobart and Griffith in northern Indiana’s...
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 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 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 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 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...
Indiana’s Panhandle Pathway follows a former Pennsylvania Railroad corridor out of Winamac south to Kenneth. Along the way, the trail links the communities of Star City, Thornhope, and Royal Center...
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The Riverside Trail winds along the west bank of the St. Joseph River for just over 3 miles in northern Indiana's South Bend. Several benches along the way allow you to take in the beautiful river...
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...
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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...
Although less than 1 mile long, the West Bank Walkway offers lovely views of the St. Joseph River in downtown South Bend. Midway, a converted railroad trestle over the waterway connects trail-goers to...
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 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...
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...
We love riding this trail. Since it does not go through a lot of Forest Preserves you do not see many pedestrians. We rode to the end point off of Willow Springs road 6/16/18 and the bridge to the start of the path was blocked with signs saying that the bridge was closed until October 2018. No warning signs up the week before.
FYI, the bridge you use to access the trail from Columbia Woods in Willow Springs was suddenly closed today, 6/16/16. The sign says bridge out 6/18 which would be Monday & would make more sense but they put concrete barriers across already anyway. You’ll have to access the trail elsewhere until they finish their bridge repairs.
For the most part, I agree with the five star reviews. It is a beautiful trail that takes you through forest, past a beautiful overlook, over bridges and has several bathroom/outhouses every 3-4 miles (located in the parking lots). I did not see horse poop as one review indicated and I was able to handle the 4-5 larger hills (I'm in my 60's so most bikers should handle them fine). The trail wasn't too busy (midweek) and you get the feeling that you are far from civilization because of the vast number of trees and open spaces. I took the advice from one reviewer and went counterclockwise around the circle. I really think that it had better runs in that direction. The only negative for me is that the trail takes you across a couple of busy roads and traffic didn't stop for bikers. My distance clocked in a 10 miles. Finally, this trail is excellent for really hot days because of all the shade. Enjoy!
This trail was perfect. I took my rollerblades with me while on vacation and skated here. It was very cool. The architecture is amazing for admiring and along a beach with things going on in the lake made for great scenery in all directions. Even took an intermission to get my feet in the sand since the trail goes on the beach. I will definitely be back on this trail next time I'm in Chicago!
Won’t be riding this again on the road bike. Fumes from roads make this not so pleasant. Sculptures and play ground for kids are great but that’s about it. Got lost when it flips to other side of river. This route is for kids on bikes, not serious cyclists. Fun all the same with the kids for sure
Coming from the uk I was pessimistic about city cycling. After getting bored of the lake front trail and north Sheridan/Green Bay road repeats this trail is a god send. Love it. Perfect for road biking and quiet(midweek) will continue to look for other trails but this one will be hard to beat.
I rode Ottawa to LaSalle. Sections of the trail were very rough. Motorbike tracks, moguls and stream remnants made the trail dangerous. The history and the washed out bridge are awesome(see photo).
Rode mid April, the trail is all asphalt. Parking in Crown Point was easy. Many busy streets to cross.
Excerpted from my blog (https://desplainesrivertrailcycling.blogspot.com/)
April 12, 2018
First ride of 2018, 42 miles down and only 1,958 to hit my annual target! The afternoon started out warm and sunny, a rare occurrence this Spring as the start of April hasn't been this cold in Chicago in 137 years with multiple snow storms! About 90 minutes into my ride the wind shifted and it was like someone turned on an air conditioner - in five minutes the temp went from high 60's to 50 degrees which is where I usually draw the line on riding 'cause it gets too cold for me.
Overall trail conditions are pretty decent with no flooding from Deerfield Road up to Independence Grove and while the trail surface is somewhat rutted from the long winter it is in reasonably good shape. One word of caution, bring plenty of water as none of the wells along the trail are open for the season and are wrapped in plastic film.
I did the circuit around Independence Grove and from a distance spotted what appeared to be two baby owls peeking out of the hole in tree. I thought it was my lucky day and quickly snapped this pic (see on blog) only to get closer and realize they were fake, the dead giveaway is the yellow glue on their feet - fake news indeed :-)
Not much in the way of color on the trail yet, it has been too cold for any spring flowers.
I lived in Hammond in 2014-2016 and this was one of the nearby trails I would frequent. Very well maintained. It doesn't hit any unique spots or destinations. Just a fine trail for a road or touring bike.
This is the perfect trail in so many ways. Quieter, with water and restrooms, all sorts of native birds and animals, places to picnic and just enjoy the great outdoors. I feel lucky to have this trail just a couple blocks from my home on the south end. Summer here we come !
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